Ethyl 2-chloroacetoacetate → Ethyl 2-anilino-4-methyl-1,3-thiazole-5-carboxylate

HRID 642311

Reaction equation

HRID 642311 reaction equation
[C:1]1([NH:7][C:8]([NH2:10])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([O:13][C:14](=[O:20])[CH:15](Cl)[C:16](=O)[CH3:17])[CH3:12]>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[S:9][C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:10][C:16]=1[CH3:17])=[O:20])[CH3:12]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 676454Phenylthiourea

Product 1

HCID 807772Ethyl 2-anilino-4-methyl-1,3-thiazole-5-carboxylateYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of phenylthiourea (5.04 g, 33.1 mmol) and 2-chloro-3-oxo-butyric acid ethyl ester (4.8 mL, 34.8 mmol) in ethanol (50 mL) was refluxed for 19 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 yellow solid (8.18 g): MS: (+) m/z 263.0 (M+1).

Workup

  1. temperaturewas refluxed for 19 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-23aa6f1f39d544a784f68fdab31785e9
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Linked notes

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