N-bromobutanimide → 4-Bromo-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester

HRID 642353노트

반응식

HRID 642353 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[S:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:14][C:8]=2[C:7]=1[OH:21])=[O:5])[CH3:2].[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([Br:22])[C:9]2[S:12][C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:14][C:8]=2[C:7]=1[OH:21])=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 684268667-Hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester

생성물 1

HCID 866173574-Bromo-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester수율 71.1%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of 7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester (2.10 g, 7.01 mmole), N-bromosuccinimide (1.31 g, 7.36 mmole) and benzoyl peroxide (84.9 mg, 0.35 mmole) in carbon tetrachloride (40 ml) was refluxed for 2 h before it was cooled to room temperature and partitioned between dichloromethane and water. The organic layer was washed with saturated aqueous sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a white solid (1.89 g). MS: (+) m/z 379.18, 381.18 (M+1, 79Br/81Br).

후처리

  1. temperaturewas refluxed for 2 h before it
  2. custompartitioned between dichloromethane and water
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane

출처 및 근거

ORD 기록
ord-3663eb51409d4d75b56112ff17353f86
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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