Methyl 2-chloroacetoacetate → Methyl 4-methyl-2-phenyl-1,3-thiazole-5-carboxylate

HRID 1419693Notes

Reaction equation

HRID 1419693 reaction equation
Cl[CH:2]([C:7]([CH3:9])=O)[C:3]([O:5][CH3:6])=[O:4].[C:10]([NH2:18])(=[S:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCO>[CH3:9][C:7]1[N:18]=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:17][C:2]=1[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 107332Methyl 2-chloroacetoacetateHCID 683563Thiobenzamide

Product 1

HCID 15832490Methyl 4-methyl-2-phenyl-1,3-thiazole-5-carboxylateYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 2-chloroacetoacetate (1.86 g, 12.4 mmol) and thiobenzamide (1.7 g, 12.4 mmol) in EtOH (50 mL) was refluxed for 18 h. The mixture was evaporated to dryness and the resulting oil was purified by flash chromatography to give methyl 4-methyl-2-phenylthiazole-5-carboxylate (1.21 g, 42%) as a colourless oil: 1H NMR (300 MHz, CDCl3) δ (TMS) 8.0-7.9 (m, 2H, arom), 7.5-7.4 (m, 3H, arom), 3.87 (s, 3H, OMe), 2.76 (s, 3H, Me-thiazole). Analysis calculated for C12H11NO2S: C 61.78; H 4.75; N 6.00; S 13.74. Found: C 61.56; H 4.71; N 5.82; S 14.61.

Workup

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

Sources & evidence

ORD record
ord-8880208697de406abddf0784ed08c305
Source dataset
uspto-grants-1999_03
Patent number
US05888941

Reaction notes

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