Thioacetamide → 3-(2,5-Dimethyl-thiazol-4-yl)-benzoic acid methyl ester

HRID 1265622Notes

Reaction equation

HRID 1265622 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]=1

Participants

3

Reactant 2

HCID 2723949ThioacetamideHCID 22139798Rac-3-(2-bromo-propionyl)-benzoic acid methyl ester

Product 1

HCID 696879213-(2,5-Dimethyl-thiazol-4-yl)-benzoic acid methyl esterYield 80.4%

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.

Workup

  1. customThe mixture was partitioned between AcOEt and H2O
  2. customthe organic layer was dried
  3. customevaporated
  4. customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-7c1dc49f9b404ab3a95a60a2efe053ca
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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