Methanethioamide → 4-(2-Methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 1400175노트

반응식

HRID 1400175 반응식
[CH:1]([NH2:3])=[S:2].[CH2:4]([O:6][C:7](=[O:20])[CH:8](Br)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])=O)[CH3:5]>CCO>[CH2:4]([O:6][C:7]([C:8]1[S:2][CH:1]=[N:3][C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])=[O:20])[CH3:5]

참가 물질

4

반응물 2

HCID 3005587MethanethioamideHCID 580160512-Bromo-3-(2-methoxyphenyl)-3-oxo-propionic acid ethyl ester

생성물 1

HCID 670764344-(2-Methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a 0° C. solution of thioformamide (prepared according to Eur. J. Med. Chem. 2004, 39, 867-872) (0.70 g, 11.5 mmol) in absolute EtOH (1 ml) was added a solution of 2-bromo-3-(2-methoxyphenyl)-3-oxo-propionic acid ethyl ester (2.4 g, 7.97 mmol) in ethanol abs. (9 ml) in drops. The reaction mixture was stirred at room temperature for 72 hours. After quenching with water and extraction with chloroform, the organics were dried over Na2SO4 and evaporated. Flash chromatography on SiO2 gel (petroleum ether/ethyl acetate, 60/40) gave crude 4-(2-methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester that was used in the next step without further purification.

후처리

  1. customAfter quenching with water and extraction with chloroform
  2. dry with materialthe organics were dried over Na2SO4
  3. customevaporated

출처 및 근거

ORD 기록
ord-1e5a69bf5c1048e7a337288a698a538d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906935B2

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