N-bromobutanimide → 4-Bromomethyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester

HRID 642304

반응식

HRID 642304 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][C:7]=1[CH3:18])=[O:5])[CH3:2].[Br:19]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[S:10][C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][C:7]=1[CH2:18][Br:19])=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 576654844-Methyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester

생성물 1

HCID 684289834-Bromomethyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester수율 101.9%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of 4-methyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester (1.31 g, 4.99 mmol), N-bromosuccinimide (905 mg, 5.08 mmol) and benzoyl peroxide (60 mg, 0.25 mmol) in carbon tetrachloride (25 mL) was refluxed for 3 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 to give the title compound as a yellow solid (1.74 g): MS: (+) m/z 342.0, 344.0 (M+1, 79Br/81Br).

후처리

  1. temperaturewas refluxed for 3 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

출처 및 근거

ORD 기록
ord-eea377ddf9ec4dca8818e281cb7dc51b
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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