Ethyl 2-chloroacetoacetate → 4-Methyl-2-(methyl-phenyl-amino)-thiazole-5-carboxylic acid ethyl ester

HRID 642307

Reaction equation

HRID 642307 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([NH2:5])=[S:4].[CH2:12]([O:14][C:15](=[O:21])[CH:16](Cl)[C:17](=O)[CH3:18])[CH3:13]>C(O)C>[CH2:12]([O:14][C:15]([C:16]1[S:4][C:3]([N:2]([CH3:1])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N:5][C:17]=1[CH3:18])=[O:21])[CH3:13]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 7236311-Methyl-1-phenylthiourea

Product 1

HCID 130483514-Methyl-2-(methyl-phenyl-amino)-thiazole-5-carboxylic acid ethyl esterYield 88.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-methyl-1-phenyl-thiourea (5.03 g, 30.3 mmol) and 2-chloro-3-oxo-butyric acid ethyl ester (4.4 mL, 31.8 mmol) in ethanol (18 mL) was refluxed for 20 h before it was cooled to room temperature and concentrated in vacuo. It was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a brown solid (7.39 g): MS: (+) m/z 277.0 (M+1).

Workup

  1. temperaturewas refluxed for 20 h before it
  2. concentrationconcentrated in vacuo
  3. customIt was partitioned between ethyl acetate and saturated sodium bicarbonate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f86698936034ec39ec323144c124c42
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Linked notes

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