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[ CAS No. 42926-52-3 ] {[proInfo.proName]}

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Chemical Structure| 42926-52-3
Chemical Structure| 42926-52-3
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Product Details of [ 42926-52-3 ]

CAS No. :42926-52-3 MDL No. :MFCD00016348
Formula : C9H9ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MDKAAWDKKBFSTK-UHFFFAOYSA-N
M.W : 184.62 Pubchem ID :3016397
Synonyms :

Safety of [ 42926-52-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H290-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 42926-52-3 ]

* 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 [ 42926-52-3 ]

[ 42926-52-3 ] Synthesis Path-Downstream   1~10

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  • [ 27578-60-5 ]
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  • 2-ethoxy-benzoic acid-(2-piperidino-ethylamide) [ No CAS ]
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  • [ 16386-47-3 ]
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  • [ 13626-20-5 ]
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  • [ 102476-73-3 ]
  • 5
  • [ 2216-51-5 ]
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  • 2-ethoxy-benzoic acid-((1<i>R</i>)-menthyl ester) [ No CAS ]
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  • [ 53715-17-6 ]
  • [ 105541-36-4 ]
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  • [ 134-11-2 ]
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YieldReaction ConditionsOperation in experiment
With thionyl chloride; for 0.666667h;Heating / reflux; 2-ethoxyl benzoic acid (10.0g, 60.2mmol) was added into thionyl chloride (20ml), and the mixture was refluxed with agitation for 40 minutes, and the excess amount of thionyl chloride was evaporated under reduced pressure. The residual was dissolved into dichloromethane (150ml). Within 30 minutes and being stirred on ice bath, the afore-obtained solution of 2-ethoxyl benzoyl chloride was dropped into the compound (1a) (7.0g, 56.8mmol) dissolved in tetrahydrofuran (80ml) and triethylamine (8.5ml, 61.0mmol). After completion, the mixture was stirred for 1 hour at 0C . After being washed with water and filtrated with diatomaceous earth, the reaction solution was mixed with 20g of silica gel and evaporated to dryness. The resulting residual was eluted with dichloromethane by using silica gel(80g) column to obtain 7.5g of solid product (3a) with the yield of 48%. Furthermore, the sample for analysis was prepared by column chromatography (developing agent: dichloromethane: n-hexane=1:2) and recrystallization (dichloromethane: n-hexane=1:5). mp 183~184C (sublimation 162C); IR (cm-1) : 3326, 3309, 2981, 2938, 2915, 2854, 2208, 1647, 1593, 1471, 1309, 1302, 1232, 1039, 923, 727, 655, 648; 1H NMR (CDCl3) : delta 1.70 (t, J=7.0Hz, 3H), 2.15 (s, 3H), 4.32 (q, J=7.0Hz, 2H), 6.24 (s, 1H), 7.04 (d, 1H), 7.10 (m, 1H), 7.51 (dd, 1H), 8.20 (dd, J=7.9 and 1.8Hz, 1H), 10.69 (brs, 1H), 10.80 (s, 1H); 13CNMR (CDCl3) : delta (CH3) 10.6, 15.0; (CH2) 65.7; (CH) 110.3, 112.3, 121.4 132.1, 134.2; (C) 78.7, 115.6, 119.2, 119.4, 136.7, 157.0, 163.2; MS (ES+) : m/z 287 (M+NH4) . Elemental analysis (C15H15N3O2) : C 66.90%; H 5.61%; N 15.60%; 0 11.88%. The compound (3b) was prepared from compound (1b) according to the above-mentioned method with the yield of 41%. mp 58~61C; IR (cm-1) : 3596, 3336, 2969, 2937, 2877, 2216, 1676, 1658, 1603, 1571, 1537, 1475, 1431, 1292, 1232, 1122, 1037, 927, 789, 752, 577; 1H NMR (CDCl3): delta 0.88 (t, J=7.4Hz, 3H), 1.58 (t, J=7.0Hz, 3H), 1.75(m, 2H), 2.16 (s, 3H), 3.73 (t, J=7.4Hz, 2H),4.30 (q, J=7.0Hz, 2H), 6.36 (s, 1H), 7.04 (d, 1H), 7.11 (m, 1H), 7.48 (dd, 1H), 8.23 (dd, J=7.9 and 1.8Hz, 1H), 9.62 (brs, 1H) ; 13C NMR (CDCl3) : delta (CH3) 11.1, 14.8; (CH2) 23.6, 48.3, 65.2; (CH) 112.5, 117.0, 121.3, 132.5, 134.1; (C) 89.2, 115.6, 119.8, 120.5, 131.2, 157.1, 165.0; MS (ES+): m/z 329 (M+NH4).
With thionyl chloride;N,N-dimethyl-formamide; In hexane; for 1h;Heating / reflux; To a stirred solution of 2-Ethoxy-6-pentadecylbenzoic Acid (6.5 g, 16 mmol) in hexane (60 mL) were added thionyl chloride (2.5 g, 21 mmol) and N,N-dimethylformamide (0.5 mL). The reaction mixture was heated to reflux for 1 h. After the reaction was complete, the solvent was evaporated under reduced pressure to yield the desired 2-Ethoxy-benzoyl Chloride, which was redissolved in dichloromethane (50 mL) and used for the condensation with anilides.
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 1h; Example 9A 2-ethoxy-N-(4-trifluoromethyl-thiazol-2-yl)-benzamide A solution of 2-ethoxybenzoic acid (0.75 g, 4.5 mmol) in 23 mL of methylene chloride at 0 C. was treated with oxalyl chloride (0.44 mL, 4.9 mmol) followed by 2 drops of dimethylformamide. The solution was stirred at ambient temperature for 1 hour and then concentrated under reduced pressure to provide 0.83 g of 2-ethoxybenzoyl chloride.
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 1h; A solution of 2-ethoxybenzoic acid (0.75 g, 4.5 mmol) in 23 mL of methylene chloride at 0 0C was treated with oxalyl chloride (0.44 mL, 4.9 mmol) followed by 2 drops of dimethylformamide. The solution was stirred at ambient temperature for 1 hour and then concentrated under reduced pressure to provide 0.83 g of 2-ethoxybenzoyl chloride
With 1-methyl-pyrrolidin-2-one; thionyl chloride; In ethyl acetate; for 1h;Reflux; Compound (16a) (10.0 g, 29.9 mmol) was added to AcOEt (100 ml), and then triethylamine (15.1 ml, 3.6 eq. ) was added thereto, followed by stirring at room temperature for one hour. The solution was cooled to about 0C. Separately, N- methylpyrrolidone (200 mu) and AcOEt (50 ml) were added to 2- ethoxybenzoic acid (5.95 g, 1.2 eq.), and then thionyl chloride (2.83 ml, 1.3 eq. ) was added thereto, followed by heating at reflux for one hour to prepare a solution of 2-ethoxybenzoyl chloride. The solution of 2-ethoxybenzoyl chloride was added at 0C to the Compound (16a) -containing solution, which had been obtained as above, followed by striing at the same temperature for 30 minutes. After the completion of the reaction, water (50 ml) and concentrated hydrochloric acid (5 ml) were added thereto, and extraction and liquid separation was performed. Subsequently, the organic layer was washed with water (50 ml) and a 25% NaOH aqueous solution (5 ml), and concentrated to dryness to obtain an oily product. EtOH (50 ml) and water (20 ml) were added to the oily product, followed by dissolution, and a seed crystal was added thereto, followed by cooling and aging. The precipitated crystals were then collected by filtration, and dried at 45C to give Compound (1a) (9.70 g) . Compound (1a): 1H NMR (CDCl3, 400 MHz) delta 1.40 (d, J = 6.0 Hz, 6H) , 1.49 (t, J = 6.9 Hz, 3H), 4.19 (q, J = 6.9 Hz, 2H) , 4.63 (d, J = 5.5 Hz, 2H) 4.69 (sept, J = 6.0 Hz, 1H) , 6.63 (t, J = 75 Hz, 1H) , 6.95 (d, J = 8.2 Hz, 1H), 7.08 (t, J = 7.8 Hz, 1H) , 7.23 (d, J = 8.2 Hz 1H) , 7.43 (td, J = 8.0, 1.4 Hz, 1H),7.59 (dd, J = 8.2, 1.8 Hz, 1H) 7.67 (d, J = 1.8 Hz, 1H) , 7.67 (s, 1H) , 8.24 (dd, J = 7.8, 1.8 Hz, 1H), 8.56 (br-s, 1H).
With thionyl chloride; N,N-dimethyl-formamide; at 20℃; for 24h; General procedure: Benzo[d][1,3]dioxole-5-carboxylic acid (8.00 g, 48.1 mmol), SOCl2 (10.4 mL, 144 mmol) and DMF (0.15 mL, 2 mmol) were mixed together in a flask protected with CaCl2 trap and stirred magnetically at r.t. After 24 h, the homogeneous mixture was diluted with toluene (100 mL) and concentrated on a rotary evaporator at 40 C; the residue was diluted with CHCl3 (20 mL) at -10 C and added dropwise to stirred aqueous ammonia (25%, 30 mL) at -10 C. The layers were separated, the aqueous layer was extracted with CHCl3 (2 × 25 mL) and the combined organic extracts were concentrated on a rotary evaporator at 20-80 C. The residue was used without further purification.
With thionyl chloride; In dichloromethane; at 100℃; for 0.5h;Cooling with ice; 1) Preparation of 2-ethoxybenzoyl chloride: lm0l 2-ethoxybenzoic acid was dissolved in methylene chloride to give 2-ethoxybenzoyl chloride at a concentration of lOOOmI / L , Ice bath conditions slowly dropping l.lmol thionyl chloride, drop after completion, 100 C refluxing reaction for 30 minutes, vacuum distillation to remove dichloromethane, 2-ethoxy benzoyl chloride, without further purification , Direct follow-up reaction;

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  • [ 100-65-2 ]
  • [ 69079-96-5 ]
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  • [ 109-89-7 ]
  • [ 3688-82-2 ]
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  • [ 108-00-9 ]
  • [ 109105-27-3 ]
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