Ethyl bromopyruvate → Ethyl 2-(4-chlorophenyl)-1,3-thiazole-4-carboxylate

HRID 1419695Notes

Reaction equation

HRID 1419695 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[S:16])=[CH:13][CH:12]=1>CCO>[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]2[S:16][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:17]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 27348264-Chlorothiobenzamide

Product 1

HCID 2799493Ethyl 2-(4-chlorophenyl)-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl bromopyruvate (354 mg, 1.8 mmol) and 4-chlorothiobenzamide (283 g, 1.65 mmol) in EtOH (40 mL) was refluxed for 3 h. The mixture was evaporated to dryness and the resulting oil was purified by flash chromatography to give ethyl 2-(4-chlorophenyl)thiazole-4-carboxylate as a colourless oil: 1H NMR (80 MHz, CDCl3) δ (TMS) 8.15 (s, 1H, thiazole), 7.95 (dt, Jt =2, Jd =8.5, 2H, arom), 7.42 (dt, Jt =2, Jd =8.5, 2H, arom), 4.45 (q, J=7, 2H, OCH2), 1.43 (t, J=7, 3H, OCH2CH3). Analysis calculated for C12H10ClNO2S: C 53.84; H 3.76; N 5.23; S 11.97. Found: C 53.65; H 3.77; N 5.23; S 11.51.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe resulting oil was purified by flash chromatography

Sources & evidence

ORD record
ord-35106c48a1e34a719bde096d52238894
Source dataset
uspto-grants-1999_03
Patent number
US05888941

Reaction notes

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