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[ CAS No. 28721-09-7 ] {[proInfo.proName]}

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Chemical Structure| 28721-09-7
Chemical Structure| 28721-09-7
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Product Details of [ 28721-09-7 ]

CAS No. :28721-09-7 MDL No. :MFCD08460125
Formula : C16H14N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PIZOFBKQWNPKDK-UHFFFAOYSA-N
M.W : 266.29 Pubchem ID :120031
Synonyms :
Chemical Name :10-Methoxy-5H-dibenzo[b,f]azepine-5-carboxamide

Calculated chemistry of [ 28721-09-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.06
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 81.94
TPSA : 55.56 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 2.45
Log Po/w (WLOGP) : 2.87
Log Po/w (MLOGP) : 2.39
Log Po/w (SILICOS-IT) : 1.65
Consensus Log Po/w : 2.34

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.35
Solubility : 0.12 mg/ml ; 0.00045 mol/l
Class : Soluble
Log S (Ali) : -3.26
Solubility : 0.146 mg/ml ; 0.000549 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.27
Solubility : 0.0142 mg/ml ; 0.0000535 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.1

Safety of [ 28721-09-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 28721-09-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 28721-09-7 ]

[ 28721-09-7 ] Synthesis Path-Downstream   1~14

YieldReaction ConditionsOperation in experiment
75% The title compound can be isolated by adding 1N NaOH to a pH of >=8 followed by extraction with toluene. Drying of the combined organic layers and concentration in vacuo yields the title compound as a light yellow solid (yield>=75%).
  • 2
  • [ 4698-11-7 ]
  • [ 917-61-3 ]
  • [ 28721-09-7 ]
YieldReaction ConditionsOperation in experiment
50% [10-METHOXY-5H-DIBENZ (B, 0AZEPINE] (29.9 g, 0.134 mol) was added to 300 ml acetonitrile in a three-neck flask (500 ml) equipped with a mechanical stirring apparatus. The mixture was stirred at room temperature for 15 minutes, and then [NAOCN] (18 g, 0.277 mol) was added, followed by pyridiniump-toluenesulfonate (75 g, 0.3 mol). The mixture was stirred at room temperature for about 4 hours, at which time TLC indicated that the reaction was complete (disappearance of [10-METHOXY-5H-DIBENZ (BAZEPINE).] 30 ml water was added, and the mixture stirred for 15 minutes. The solids were filtered and the filtrate was concentrated under vacuum. The semi-solid residue was triturated with acetone to provide a creamy solid, which was dried at [80] C to provide 18 g (0.068 mol, 50% yield) of [10-METHOXY-5H-DIBENZ [B2FLAZEPINE-5-CARBOXAMIDE (10-METHOXYCARBAMAZEPINE).]
In a three-neck flask (500 ml), equipped with a mechanical stirring apparatus, 15 ml water was introduced, followed by pyridinium bromide (71.75 g, 0.45 mole; Chemadaa' (Nir Yitshak, Israel) ). The mixture was stirred at room temperature [(22 C)] for about 10 minutes. Then 250 ml toluene was added, followed by 50 g (0.224 mol) of [10-METHOXY-5H-] dibenz [[BZF] AZEPINE] (compound of formula (4), wherein R4 is methoxy). [Note: 10-methoxy-5H- dibenz [[B, T] AZEPINE] may be obtained from [IMINOSTILBENE] according to the process disclosed in U. S. Patent No. 5,808, 058. [10-METHOXY-5H-DIBENZ [B FLAZEPINE] also is commercially available from various suppliers, including Zhejiang Jiuzhou Pharmaceutical Co. , Ltd. (Zhejiang, China), and Ningbo Chongyangtang Biologic Tech Co. , Ltd. (Ningbo, China)] [NAOCN] (45 g, 0.69 mol ; OCI Corp. , South Korea) was added and the reaction was mixed for about 7-8 hours at room temperature [(22C).] After [7-8] hours, [125ML] of water was added, and the mixture was stirred for about 15 minutes. The resulting solid carbamate of formula (1), 10-methoxy-5H- dibenz [[B2TAZEPINE-5-CARBOXAMIDE,] was filtered and washed with 50 ml of water. The organic layer was separated and washed with water (2 x [50ML).] In a 500 ml three necked flask, the organic phase from above was introduced, to which the solid carbamate of formula (1) [(10-METHOXY-5H-DIBENZ [B2FLAZEPINE-5-CARBOXAMIDE)] was added to form a slurry. The mixture was heated to 89 C to clarify the solution, and 250 ml of 10% [HC1] was added dropwise with stirring. When thin layer chromatography indicated that the intermediate carbamate of formula (1) had been substantially consumed, the reaction mixture was cooled to room temperature and the mixture was stirred at this temperature for 15-30 minutes. The product, [10-OXO-10,] [11-DIHYDRO-5H-DIBENZ [B2FLAZEPINE-5-CARBOXAMIDE] (oxcarbazepine), was filtered and the crude oxcarbazepine cake was thoroughly washed with water until the pH reached 6-7. The mixture was then washed with toluene (50 ml), and the solids were dried to yield 34.4 g (0.137 mol) crude oxcarbazepine as a yellow-brown powder (yield relative to (2) is [61%).] The crude oxcarbazepine was slurried in 408 ml of boiling 80: 20 isopropanol : water for about 1 hour. The solid was separated by filtration and dried to afford 30.6 g oxcarbazepine [(89%] purification yield). Further purification was carried out in 765 ml of boiling 80: 20 isopropanol: water, hot filtration and cooling to room temperature. Filtration and drying of the solid precipitate afforded 26.5 g of purified oxcarbazepine (yield relative to starting material (2) is 47%, and purification yield is 87%).; The carbamoylation reaction was performed as in Example 1, except that [150] ml toluene was used instead of 250 ml. The resulting solid carbamate of formula (1), 10-methoxy-5H- dibenz [[B2FLAZEPINE-5-CARBOXAMIDE,] was isolated as described in Example 1. In a three necked flask, 330 ml of isopropyl alcohol, 78 ml of 12% HCl, and the solid 10- [METHOXY-SH-DIBENZ [B2FLAZEPINE-S-CARBOXAMIDE] were introduced. The mixture was heated to [78] [- 82 C] for about 1 hour. When TLC indicated that the carbamate of formula (1) was consumed, the reaction mixture was cooled to room temperature and stirred for 1 hour. The separated solids were filtered and washed with water to provide crude 10-oxo-10, [11-DIHYDRO-SH-DIBENZ [BFLAZEPINE-S-] carboxamide (oxcarbazepine), which was purified as described in Example 1. Yield relative to starting material of formula (2) was 43-45%.
With maleic acid; In dichloromethane; at 20 - 45℃; for 6 - 24h; EXAMPLE 1A Preparation of 10-methoxycarbamazepine To a 1 L 4-necked round bottom flask was added 10.0 g (0.045 mol) of 10-methoxyiminostilbene, 150.0 ml of dichloromethane, 37.0 g (0.57 mol) of sodium cyanate and 15.0 g (0.13 moles) of maleic acid and stirred at room temperature. The contents were heated to reflux (40-45 C.) under vigorous stirring for about 6 to about 8 hours. After completion of the reaction (detected by TLC) the reaction mass was filtered and washed with 50.0 ml dichloromethane. The dichloromethane layer was washed with water (50.0 ml*2) and the layers were separated. EXAMPLE 2A Preparation of 10-methoxycarbamazepine 50.0 g (0.224 moles) of 10-methoxyiminostilbene was dissolved in 750.0 ml of dichloromethane. 185.0 g (2.846 moles) of sodium cyanate and 75.0 g (0.65 moles) of maleic acid were added to the above solution at a temperature ranging from about 25 C. to about 30 C. The reaction mass was stirred for about 24 hours. After completion of the reaction (determined by HPLC/TLC) the reaction mass was filtered and washed three times with 100 mL of dichloromethane. The dichloromethane layer was evaporated to get a residue of about 150 g to about 200 g.
With MANDELIC ACID; In dichloromethane;Reflux;Product distribution / selectivity; EXAMPLE-2: Preparation of Oxcarbazepine; a) Preparation of 10-methoxy carbamazepine from 10-methoxyiminostilbene; A suspension of 10 g of 10-methoxyiminostilbene in 250 ml dichloromethane was -30 treated with 17.5 g of sodium cyanate and 24 g of mandelic acid and was heated to reflux for about 6-8 hrs. The reaction mixture was cooled to room temperature and the reaction mixture was washed with distilled water and aqueous sodium bicarbonate and further the organic layer was distilled off completely. The resulting residue was treated with with isopropanol, separated solid was filtered and dried to give g of35 10-methoxy carbamazepine.
Example 5; Preparation of 10-oxo-lOJ l-dihydro-5H-dibenz[6,/]azepine-5-carboxamide (Oxcarbazepine), compound of formula [I]; 10-Methoxyiminostilbene, compound of formula [XX], (100 g) was dissolved in toluene (1000 ml). Sodium cyanate (100 g) and benzoic acid (190 g) were added and the reaction mixture was vigorously stirred and heated at 85-90C for 1O h. After the reaction completion, the reaction mixture was cooled, followed by the addition of aqueous NaOH solution (10%, 800 ml) to pH 11. The reaction mixture was stirred for 3 h at this temperature followed by cooling to 0-50C. The reaction mixture was filtered and washed with toluene and water and dried to give the compound of formula [XXI] (yield = 110 g).
With MANDELIC ACID; In dichloromethane; at 20℃; for 8h;Reflux;Product distribution / selectivity; a) Preparation of 10-methoxy carbamazepine from 10-methoxyiminostilbene A suspension of 10 g of 10-methoxyiminostilbene in 250 ml dichloromethane was treated with 17.5 g of sodium cyanate and 24 g of mandelic acid and was heated to reflux for about 6-8 hrs. The reaction mixture was cooled to room temperature and the reaction mixture was washed with distilled water and aqueous sodium bicarbonate and further the organic layer was distilled off completely. The resulting residue was treated with with isopropanol, separated solid was filtered and dried to give g of 10-methoxy carbamazepine.

  • 3
  • [ 28721-09-7 ]
  • [ 28721-07-5 ]
YieldReaction ConditionsOperation in experiment
73.0% With hydrogenchloride; In water; at 25 - 85℃; for 4 - 6h; To the organic layer resulting from Example 1A was added 2N HCl (50.0 ml) and the reaction mass was maintained at a temperature ranging from about 40 C. to about 50 C. for about 4 to about 6 hours. After completion of the reaction (detected by TLC) the reaction mass was cooled to a temperature ranging from about 0 C. to about 5 C. for about one hour and the separated solids were filtered and washed with dichloromethane (15.0 ml). Purification: To a 3 L 4-necked round bottom flask was added 1125 ml of methanol and 75 gm crude oxcarbazepine prepared by the process of Example 1B and stirred at room temperature, about 25 C. to about 30 C. The reaction mass slurry was heated to reflux, a temperature of about 65 C., and further stirred for about 30 to about 40 minutes. 450 ml acetic acid was added under reflux which resulted in a clear solution. The solution was stirred under reflux at a temperature of about 70 C. for about 30 to about 40 minutes. 7.5 g of charcoal was added to the solution and stirred under reflux for about 20 to about 30 minutes. The reaction mass was filtered and washed twice in a hyflow bed with 75 ml of acetic acid and methanol in a 2:5 ratio at a temperature of about 70 C. The filtrate was cooled in a 3 L 4-necked round bottom flask to a temperature of about 30 C. for about 1 hour, and further cooled to a temperature of about 0 C. for about 30 min. The precipitated product was filtered and dried to get pure oxcarbazepine. Yield=73.0%, m.p. 222 C., purity>99.5%, 1H NMR Spectrum (CDCl3, TMS as internal standard) shows 6 at 3.3 (1H,d), 4.4(1H,d), 5.0(2H.br.s), 7.2-8.2 (8H,m&d).EXAMPLE 2B Preparation of Oxcarbazepine The residue obtained in Example 2A was transferred to a 2 L 4-necked round bottom flask and 500 ml of 2N aqueous HCl was added at a temperature ranging from about 25 C. to about 30 C. The reaction mass was heated to a temperature ranging from about 80 C. to about 85 C. and maintained for between 4 to 5 hours. After completion of the reaction (detected by HPLC/TLC), the reaction mass was cooled to a temperature ranging from about 50 C., and 500 ml of toluene was charged to the reaction mass and maintained for 30 minutes at a temperature of about 50 C. The reaction mass was further stirred at a temperature ranging from about 25 C. to about 30 C. for about 30 minutes. The solids were filtered, separated, and then washed twice with 100 ml of toluene. The product was dried to get crude oxcarbazepine of 97-98% purity as determined by HPLC. Purification: The purification of the oxcarbazepine prepared in Example 2A was carried in substantially the same manner as in Example 1.
With hydrogenchloride; In water; toluene; at 20 - 89℃; for 0.25h; In a three-neck flask (500 ml), equipped with a mechanical stirring apparatus, 15 ml water was introduced, followed by pyridinium bromide (71.75 g, 0.45 mole; Chemadaa' (Nir Yitshak, Israel) ). The mixture was stirred at room temperature [(22 C)] for about 10 minutes. Then 250 ml toluene was added, followed by 50 g (0.224 mol) of [10-METHOXY-5H-] dibenz [[BZF] AZEPINE] (compound of formula (4), wherein R4 is methoxy). [Note: 10-methoxy-5H- dibenz [[B, T] AZEPINE] may be obtained from [IMINOSTILBENE] according to the process disclosed in U. S. Patent No. 5,808, 058. [10-METHOXY-5H-DIBENZ [B FLAZEPINE] also is commercially available from various suppliers, including Zhejiang Jiuzhou Pharmaceutical Co. , Ltd. (Zhejiang, China), and Ningbo Chongyangtang Biologic Tech Co. , Ltd. (Ningbo, China)] [NAOCN] (45 g, 0.69 mol ; OCI Corp. , South Korea) was added and the reaction was mixed for about 7-8 hours at room temperature [(22C).] After [7-8] hours, [125ML] of water was added, and the mixture was stirred for about 15 minutes. The resulting solid carbamate of formula (1), 10-methoxy-5H- dibenz [[B2TAZEPINE-5-CARBOXAMIDE,] was filtered and washed with 50 ml of water. The organic layer was separated and washed with water (2 x [50ML).] In a 500 ml three necked flask, the organic phase from above was introduced, to which the solid carbamate of formula (1) [(10-METHOXY-5H-DIBENZ [B2FLAZEPINE-5-CARBOXAMIDE)] was added to form a slurry. The mixture was heated to 89 C to clarify the solution, and 250 ml of 10% [HC1] was added dropwise with stirring. When thin layer chromatography indicated that the intermediate carbamate of formula (1) had been substantially consumed, the reaction mixture was cooled to room temperature and the mixture was stirred at this temperature for 15-30 minutes. The product, [10-OXO-10,] [11-DIHYDRO-5H-DIBENZ [B2FLAZEPINE-5-CARBOXAMIDE] (oxcarbazepine), was filtered and the crude oxcarbazepine cake was thoroughly washed with water until the pH reached 6-7. The mixture was then washed with toluene (50 ml), and the solids were dried to yield 34.4 g (0.137 mol) crude oxcarbazepine as a yellow-brown powder (yield relative to (2) is [61%).] The crude oxcarbazepine was slurried in 408 ml of boiling 80: 20 isopropanol : water for about 1 hour. The solid was separated by filtration and dried to afford 30.6 g oxcarbazepine [(89%] purification yield). Further purification was carried out in 765 ml of boiling 80: 20 isopropanol: water, hot filtration and cooling to room temperature. Filtration and drying of the solid precipitate afforded 26.5 g of purified oxcarbazepine (yield relative to starting material (2) is 47%, and purification yield is 87%).
With hydrogenchloride; In water; isopropyl alcohol; at 20 - 82℃; for 2h; The carbamoylation reaction was performed as in Example 1, except that [150] ml toluene was used instead of 250 ml. The resulting solid carbamate of formula (1), 10-methoxy-5H- dibenz [[B2FLAZEPINE-5-CARBOXAMIDE,] was isolated as described in Example 1. In a three necked flask, 330 ml of isopropyl alcohol, 78 ml of 12% HCl, and the solid 10- [METHOXY-SH-DIBENZ [B2FLAZEPINE-S-CARBOXAMIDE] were introduced. The mixture was heated to [78] [- 82 C] for about 1 hour. When TLC indicated that the carbamate of formula (1) was consumed, the reaction mixture was cooled to room temperature and stirred for 1 hour. The separated solids were filtered and washed with water to provide crude 10-oxo-10, [11-DIHYDRO-SH-DIBENZ [BFLAZEPINE-S-] carboxamide (oxcarbazepine), which was purified as described in Example 1. Yield relative to starting material of formula (2) was 43-45%.
With o-toluenesulfonic acid; In 1,2-dichloro-ethane; at 20 - 80℃; for 4h; Step 3 Preparation of cxcarbazepine-from 10-Methoxy-5H-dibenz (b, f) azepine 5- carboxamide 85 gm of 10-Methoxy-5H-dibenz [b, fj azepine-5-carboxamide is dissolved in 425 ml of ethylene dichloride. To this 800 mi of 2N o-toluene sulfonic acid is added and heated to 75-80C & maintained for bout 3 hours. It is then cooled to 20C & maintained for about 1 hour. The product oxcarbazepine is separated by filtration. This is then purified in acetone-water to yield 55 gms of pure oxcarbazepine.
Preparation of oxcarbazepine (I) 600 ml of water are added to the round-bottomed flask containing the suspension of 10- methoxy-5H-dibenzo [b, faazepine-5-carboxamide (IV) from Example 1, and about 12 g of 37% HC1 are added dropwise to pH = 1. The suspension is stirred at about 95 DEG C for 4 hours. The mixture is cooled to 25 DEG C and about 14 g of 30% NaOH are added dropwise to bring the pH from 1.0 to 7.0-7. 5. The reaction suspension is filtered at 25 DEG C and the cake is washed twice with water (2 x 100 ml), the filtration and washing waters then being removed. The cake is washed three times with methanol (3 x 100 ml) at 12-14 DEG C and the waters are then removed. The wet cake (160-170 g) is suspended in dimethylacetamide (400 ml) while heating at 110 DEG C until the solid has dissolved. The product is filtered off at a temperature above 80 DEG C (temperature of start of recrystallization). The filtrate is cooled to 60 DEG C, 400 ml of methanol are then added to the suspension, and the resulting mixture is cooled first to 25 DEG C and then to 0-5 DEG C. After 1 hour at 0-5 DEG C, the cake is washed with 150 ml of methanol at 12-14 DEG C and the methanolic washing phase is removed. The cake is dried under vacuum at 40 DEG C for 6 hours.
With water; oxalic acid; at 90℃; for 17h;Product distribution / selectivity; b) Preparation of Oxcarbazepine from 10-methoxy carbamazepine; 100 g of <strong>[28721-09-7]10-methoxycarbamazepine</strong> in 1000 ml water and 69.24 g of oxalic acid solution was heated to 9O0C and maintained for about 17 hrs. After completion of the reaction the reaction mixture was cooled to room temperature (RT). The resulting reaction mass was filtered and washed with 1000 ml of DM water. The wet material obtained was charged with isopropyl alcohol and DM water. The obtained reaction mixture was heated to reflux for about 2 h. the reaction mixture was cooled to 15- 250C, filtered and washed with 100 ml of IPA-water mixture. The resulting compound is dried at 6O0C for 6 h to produce 90 g of Oxcarabzepine.
With hydrogenchloride; In methanol; water; at 75 - 80℃; The crude [XXI] was taken in a RB flask and methanol (600 ml) was added. The reaction mixture was heated to reflux. The reaction mixture was cooled, methanol was distilled off and toluene (50 ml) was added and further distilled. The residual [XXI] was cooled and toluene (500 ml) was added and stirred. Water was added followed by addition of cone. HCl. The reaction mixture was heated at 75-80C. The reaction mixture was cooled and the crude oxcarbazepine [I] was filtered, washed with toluene, 5% NaHCO3 and DM water and vacuum dried to give crude oxcarbazepine of formula[I] (yield = 82 g). The oxcarbazepine thus formed can be purified by dissolving in methanol (600 ml). The reaction mixture was stirred for 15-20 min. The pH of the <n="16"/>reaction mixture was maintained in the range of 7.5-8.5. The reaction mixture was stirred and heated to reflux at 65-70C for 2 h, and cooled, filtered and washed with methanol and dried to give oxcarbazepine [I], which was further purified by heating in methanol (1400 ml) and dichlormethane (1400 mL). The reaction mixture was refluxed for 30 min and treated with activated carbon. The reaction mixture was filtered through Hyflo bed and washed with methanol and dichloromethane mixture (1:1). The solvent was distilled to residual volume of 1000 mL. The reaction mixture was cooled and maintained. The reaction mixture was filtered through buchner funnel and washed with methanol and dried under vacuum at 50-60C to give pure oxcarbazepine (90 g).
With water;oxalic acid; at 90℃; for 19h;Reflux;Product distribution / selectivity; b) Preparation of Oxcarbazepine from 10-methoxy carbamazepine 100 g of <strong>[28721-09-7]10-methoxycarbamazepine</strong> in 1000 ml water and 69.24 g of oxalic acid solution was heated to 90 C. and maintained for about 17 hrs. After completion of the reaction the reaction mixture was cooled to room temperature (RT). The resulting reaction mass was filtered and washed with 1000 ml of DM water. The wet material obtained was charged with isopropyl alcohol and DM water. The obtained reaction mixture was heated to reflux for about 2 h. the reaction mixture was cooled to 15-25 C., filtered and washed with 100 ml of IPA-water mixture. The resulting compound is dried at 60 C. for 6 h to produce 90 g of Oxcarabzepine.

  • 9
  • [ 731851-94-8 ]
  • [ 28721-09-7 ]
  • 10
  • 10-oxo-10,11-dihydro-dibenzo[<i>b</i>,<i>f</i>]azepine-5-carboxylic acid phenyl ester [ No CAS ]
  • [ 28721-09-7 ]
  • 11
  • [ 28721-08-6 ]
  • [ 28721-09-7 ]
YieldReaction ConditionsOperation in experiment
With ammonia; In methanol; for 2h;Heating / reflux; Step 2. Preparation of 10-Methoxy-5H-dibenz [b, f] azepine-5-carboxamide from 10- Methoxy-5H-dibenz [b, f] azepine-5-carbonyl chloride 100 gm of 10-Methoxy-5H-dibenz [b, f] azepine-5-carbonyl chloride is refluxed in 500 m . methanol. Dry ammonia is-passed into the boiling solution for 2 hours. The methanol is distilled water added and the reaction mixture is cooled to 25-30C and filtered. Yield of 10-Methoxy-5H-dibenz [b, f] azepine-5-carboxamide is 82 g.
With ammonia; In methanol; water; at 50℃; for 1h; The solution is heated to 50 DEG C, 300 ml of 28% aqueous ammonia (2.11 mol) are added dropwise to the homogeneous solution, and the mixture is stirred at 50 DEG C for 1 hour. HPLC monitoring after 1 hour indicates that the reaction is complete, and the solvent is partially distilled off at 40 DEG C under vacuum, down to a residual volume of about 400 ml. The solution at 25 DEG C becomes turbid due to precipitation of 10-methoxy-5H- dibenzo [b, f] azepine-5-carboxamide (IV), and the suspension thus formed is used without further purification in the following step.
  • 12
  • [ 590-28-3 ]
  • [ 4698-11-7 ]
  • [ 28721-09-7 ]
  • 13
  • [ 4698-11-7 ]
  • [ 32315-10-9 ]
  • [ 28721-09-7 ]
YieldReaction ConditionsOperation in experiment
85% ) A solution of 66.9 g (0.3 mols) of 10-methoxy-iminostilbene and 34.92 g (0.34 mols) of triethylamine in 800 ml of toluene is gradually added, during 6 hours and at a temperature of 10-15C, with a solution of 32.67 g (0.11 mols) of triphosgene in 300 ml of toluene. After completion of the reaction (disappearance of methoxy-iminostilbene) 200 ml of 30% aqueous ammonia are added gradually, vigorously stirring at room temperature for some hours. After that, the phases are separated, the toluene phase is washed with water and evaporated to dryness under reduced pressure. Yield: 69.0 g (85% on theoretical) of 10-methoxy-N-aminocarbonyl-iminostilbene (V) of purity higher than 95%.
  • 14
  • C16H14ClNO3 [ No CAS ]
  • [ 28721-09-7 ]
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10,11-Dihydro-5H-dibenzo[b,f]azepine-5-carboxamide

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Chemical Structure| 54582-35-3

[ 54582-35-3 ]

1-(4-Methoxybenzyl)urea

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Amines

Chemical Structure| 36507-30-9

[ 36507-30-9 ]

1aH-Dibenzo[b,f]oxireno[2,3-d]azepine-6(10bH)-carboxamide

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Chemical Structure| 29331-92-8

[ 29331-92-8 ]

10-Hydroxy-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide

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Chemical Structure| 89026-59-5

[ 89026-59-5 ]

4-(4-Methoxyphenyl)piperazine-1-carboxamide

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Chemical Structure| 3526-43-0

[ 3526-43-0 ]

N-(4-Methoxybenzyl)aniline

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Chemical Structure| 3564-73-6

[ 3564-73-6 ]

10,11-Dihydro-5H-dibenzo[b,f]azepine-5-carboxamide

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Related Parent Nucleus of
[ 28721-09-7 ]

Other Aromatic Heterocycles

Chemical Structure| 36507-30-9

[ 36507-30-9 ]

1aH-Dibenzo[b,f]oxireno[2,3-d]azepine-6(10bH)-carboxamide

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Chemical Structure| 29331-92-8

[ 29331-92-8 ]

10-Hydroxy-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide

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Chemical Structure| 618910-07-9

[ 618910-07-9 ]

8-Methoxy-5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

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Chemical Structure| 3564-73-6

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10,11-Dihydro-5H-dibenzo[b,f]azepine-5-carboxamide

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Chemical Structure| 62208-68-8

[ 62208-68-8 ]

Benzofuro[3,2-d]pyrimidine-2,4(1H,3H)-dione

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; ;