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

HRID 642332Notes

Reaction equation

HRID 642332 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[S:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20](=[O:26])[CH:21](Cl)[C:22](=O)[CH3:23])[CH3:18]>C(O)C>[CH2:17]([O:19][C:20]([C:21]1[S:13][C:12]([C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:16][CH:15]=2)=[N:14][C:22]=1[CH3:23])=[O:26])[CH3:18]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 27603534-Phenoxythiobenzamide

Product 1

HCID 684263914-Methyl-2-(4-phenoxy-phenyl)-thiazole-5-carboxylic acid ethyl esterYield 93.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-phenoxy-thiobenzamide (1.02 g, 4.43 mmole) and 2-chloro-3-oxo-butyric acid ethyl ester (625 μl, 4.52 mmole) in ethanol (15 ml) was refluxed for 18 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 (1.41 g). MS: (+) m/z 340.07 (M+1).

Workup

  1. temperaturewas refluxed for 18 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-0a1c49b6df3d4afdb6b0eb3c591cc126
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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