N-bromobutanimide → 4-Bromomethyl-2-(4-methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 642294

反応式

HRID 642294 の反応式
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:19])=[O:5])[CH3:2].[Br:20]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]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH2:19][Br:20])=[O:5])[CH3:2]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 7540952Ethyl 2-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

生成物 1

HCID 684274184-Bromomethyl-2-(4-methoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester収率 94.3%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 2-(4-Methoxy-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (1.41 g, 5.09 mmol), N-bromosuccinimide (951 mg, 5.34 mmol) and benzoyl peroxide (62 mg, 0.25 mmol) in carbon tetrachloride (20 mL) was refluxed for 15 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 (1.71 g): MS: (+) m/z 355.96, 357.96 (M+1, 79Br/81Br).

後処理

  1. temperaturewas refluxed for 15 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

出典と根拠

ORDレコード
ord-084115644596457d9a8a75ade597e29d
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

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