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

HRID 642307

반응식

HRID 642307 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1f86698936034ec39ec323144c124c42
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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