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With sodiumsulfide nonahydrate; acetic acid; In N,N-dimethyl-formamide; at 100℃; for 8h;
In a parallel synthesizer reaction tube, 0.40 mmol was added 2,2' -dithio diphenylamine, 0.80 mmol of p-methylbenzaldehyde, 0.20 mmol of Na2S · 9H20 and 0.20 mmol of AcOH, Then, 3 mL of DMF was added as the reaction solvent, and the reaction was stirred at 100 C for 8 hours. LC detection found that the reaction of disulfide material completely, cooled to room temperature, The solvent was removed under reduced pressure using a rotary evaporator to give the crude product. The crude product was eluted with petroleum ether and ethyl acetate as eluant and subjected to column elution (200-300 mesh silica gel) to give 175 mg of white powder 2- (4-methylphenyl) benzothiazole having a purity of more than 99%, the separation yield was 97% and the melting point was 84-86 C.
97%
General procedure: 2,2′-Disulfanediyldianiline or 5,5′-dichloro-2,2′-dithiobisaniline (0.4mmol), corresponding aryl aldehydes (0.8mmol), Na2S·9H2O (0.2mmol), and NaHCO3 or AcOH (0.2mmol) in DMF (3mL) were put into a reaction tube of parallel reactor (Wattecs). The reaction mixture was stirred at 100C under N2 atmosphere for the indicated time until the starting materials was consumed completely as monitored by TLC and LC-MS analysis. The reaction mixture was then washed with aqueous sodium bisulfite solution to remove the excess aldehyde and extracted with CH2Cl2. The organic layers were dried over anhydrous MgSO4. After filtering to remove the MgSO4, the solvent was removed under reduced pressure. The crude product was purified by column chromatography through a silica-gel column to afford the desired products.
87%
With sodium hydrogen sulfide; at 190℃; for 0.333333h;Microwave irradiation; Green chemistry;
General procedure: 2,2-Disulfanediyldianiline (1a) or 5,5-dichloro-2,2-dithiobisaniline (1b) (0.50 mmol), the corresponding aldehydes(2a-p) (1.1 mmol), NaSH (0.3 mmol) and PEG-300 (2 mL) wereput into a round-bottomed ask, and the reaction mixture wasirradiated for 20 min at 25 W. After completion of the reactionmonitored by TLC with a mixture of petroleum ether and ethylacetate as eluent, the mixture was allowed to cool to roomtemperature. Distilled water (25 mL) was added into the ask,and then the solid was precipitated from the aqueous phaseafter stirring by magnetic stirrers in 5 min. The solid precipitatewas isolated by fltration, washed twice by distilled water (5 mL)and dried for 3 h. The pure targetproducts3a-3o were obtaineddirectly. The pure products 3p and 3q were obtained by columnchromatography(PE/EtOAc as eluent).Complete characterization of the products (all known) is found in the SupplementalMaterials (Figures S 1-S 34).
84%
With sodiumsulfide nonahydrate; carbon dioxide; In water; at 50 - 80℃; for 24h;Autoclave;
(1) Synthesis of 2- (4-methylphenyl) benzothiazoleWas added to the autoclave 0.40mmol 2,2'-dithiobis aniline, 0.80mmol of methyl benzaldehyde and 0.2mmol of Na2S · 9H2O, placed magneton, then add 2mL of water as a reaction solvent, after heating to 50 2MPa charged carbon dioxide gas. And continue to heat to 80 After stirring for 24h, LC detected disulfide starting material the reaction was complete, cooled to room temperature, using a rotary evaporator to give the crude product obtained after the solvent was removed under reduced pressure. The crude product with petroleum ether and ethyl acetate as the eluent, using a gradient elution by column chromatography (200-300 mesh silica gel) was obtained with a purity greater than 99% of the white powder of 2- (4-methylphenyl ) benzothiazole 151.2mg, isolated in 84% yield,
76%
With tert.-butylhydroperoxide; copper dichloride; In chloroform; water; at 80℃; for 24h;Inert atmosphere; Schlenk technique;
A 25 mL reaction vessel was charged with 2,2'-disulfanediyldianiline 7 (0.483 mmol, 0.57 equiv), p-methylbenzaldehyde 2a (0.845 mmol), CuCl2 (0.254mmol, 0.3 equiv), tert-butylhydroperoxide (0.507 mmol, 0.6 equiv, 70% aqueous solution) and 0.1 mL CHCl3 under nitrogen. The reaction mixture was stirred in an ice bath for 30 min, andthen stirred at 80C for 24 h. After cooling to room temperature, the mixture was purified by column chromatography using silica gel (petroleum ether/ethylacetate) to afford the product 3a.
General procedure: 2,2'-Disulfanediyldianiline 1a or 6,6'-disulfanediylbis(3-chloroaniline) 1b (0.5 mmol) and carboxylic acid (1.0 mmol, except 0.5mmol for 2k) were added to a three-neck flask under an atmosphere of Ar, and 5 mL dry toluene was added, then the mixture was stirred for 2.5 h at 70 C to allow the solid to dissolve in toluene solvent completely. After the reaction solution was cooled down to 30 C, PCl3 (1.2 mmol, 0.165 g) was added dropwise. When the PCl3 was added completely, the reaction mixture was further stirred for 4 - 6 h at 100C until no 2,2'-disulfanediyldianiline or 6,6'-disulfanediylbis(3-chloroaniline) was detected by TLC analysis. The reaction solution was washed with saturated aqueous sodium bicarbonate solution and extracted with CH2Cl2. The collected organic layers were dried over anhydrous MgSO4. After filtered toremove the MgSO4 and the solvent was removed under reduced pressure. The crude product was purifiedby flash chromatography on silica gel using PE / EtOAc.
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