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

HRID 642307

反応式

HRID 642307 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1f86698936034ec39ec323144c124c42
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

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