Methanethioamide → 3-(5-Methyl-thiazol-4-yl)-benzoic acid methyl ester

HRID 1265620Notes

Reaction equation

HRID 1265620 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.[CH:16]([NH2:18])=[S:17]>CCO>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:18]=[CH:16][S:17][C:11]=2[CH3:12])[CH:5]=1

Participants

4

Reactant 2

HCID 3005587MethanethioamideHCID 22139798Rac-3-(2-bromo-propionyl)-benzoic acid methyl ester

Product 1

HCID 696892723-(5-Methyl-thiazol-4-yl)-benzoic acid methyl esterYield 103.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of crude rac-3-(2-bromo-propionyl)-benzoic acid methyl ester (2.71 g) and thioformamide (1.83 g) in EtOH (20 ml) was heated at reflux for 1 h. The mixture was partitioned between AcOEt and brine, 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-(5-methyl-thiazol-4-yl)-benzoic acid methyl ester (2.41 g) as white solid.

Workup

  1. temperatureat reflux for 1 h
  2. customThe mixture was partitioned between AcOEt and brine
  3. customthe organic layer was dried
  4. customevaporated
  5. customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-8956c7edb5fb4156b7f7c6f7c2d66b5f
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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