Ethanol → 3-Thiazol-4-yl-benzoic acid methyl ester

HRID 1265611Notes

Reaction equation

HRID 1265611 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]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 27568353-(2-bromoacetyl)benzoic AcidHCID 3005587Methanethioamide

Product 1

HCID 696880593-Thiazol-4-yl-benzoic acid methyl ester

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)+].

Workup

  1. customThe mixture was partitioned between AcOEt and brine
  2. customthe organic layer was dried
  3. customevaporated
  4. dissolutionThe residual oil was dissolved in a mixture of MeOH (20 mL)
  5. concentrationthe solution was concentrated in vacuum
  6. additiondiluted with AcOEt
  7. washwashed with sat. NaHCO3 solution and brine
  8. customdried
  9. customevaporated
  10. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-0e5bb50fdc0a4472908fd6afad97d366
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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