Ethanol → 3-Thiazol-4-yl-benzoic acid methyl ester
Reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])=O.[CH:14]([NH2:16])=[S:15].[CH3:17]CO>>[CH3:17][O:10][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][CH:13]=[C:5]([C:3]2[N:16]=[CH:14][S:15][CH:2]=2)[CH:6]=1Participants
4
Procedure
A solution of 3-(2-bromo-acetyl)-benzoic acid (1.22 g) and thioformamide (0.46 g) in EtOH (5 mL) was heated to 80° C. for 1 h. The mixture was partitioned between AcOEt and brine and the organic layer was dried and evaporated. The residual oil was dissolved in a mixture of MeOH (20 mL) and 4NHCl/Et2O (5 mL). After being kept at 20° C. for 18 h, the solution was concentrated in vacuum, diluted with AcOEt, washed with sat. NaHCO3 solution and brine, dried and evaporated. The residue was chromatographed on silica gel using AcOEt/hexane (1:3) as eluent to give 3-thiazol-4-yl-benzoic acid methyl ester (0.98 g) as off-white solid, MS (ISP) 220.2 [(M+H)+].