Thioacetamide → 3-(2,5-Dimethyl-thiazol-4-yl)-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH:11](Br)[CH3:12])[CH:5]=1.[C:16]([NH2:19])(=[S:18])[CH3:17]>>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:19]=[C:16]([CH3:17])[S:18][C:11]=2[CH3:12])[CH:5]=1Participants
3
Conditions
- Temperature
- 130 °C
Procedure
A mixture of rac-3-(2-bromo-propionyl)-benzoic acid methyl ester (6.78 g) and thioacetamide (5.63 g) was heated to 130° C. for 20 min. The mixture was partitioned between AcOEt and H2O, the organic layer was dried and evaporated and the residual oil was chromatographed on silica gel using AcOEt/hexane (1:4) as eluent to give 3-(2,5-dimethyl-thiazol-4-yl)-benzoic acid methyl ester (4.97 g) as yellow oil.