N-bromobutanimide → HCID 58610288、化合物

HRID 642290ノート

反応式

HRID 642290 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]([Cl:17])=[CH:13][CH:12]=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]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH2:18][Br:19])=[O:5])[CH3:2]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 2743519Ethyl 2-(4-chlorophenyl)-4-methyl-1,3-thiazole-5-carboxylate

生成物 1

HCID 58610288HCID 58610288、化合物収率 100.9%

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-chloro-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (2.50 g, 8.88 mmol), N-bromosuccinimide (2.13 g, 12.0 mmol) and benzoyl peroxide (150 mg, 0.62 mmol) in carbon tetrachloride (50 mL) was refluxed for 24 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 (3.23 g, product is 69% pure by 1H NMR, impurities are starting material and dibromonated compound): 1H NMR (CDCl3, 200 MHz): δ=7.90 (d, 2H), 7.44 (d, 2H), 4.96 (s, 3H), 4.38 (q, J=7.0 Hz, 2H), 1.44 (t, J=7.0 Hz, 3H).

後処理

  1. temperaturewas refluxed for 24 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-dcc7b2b7e49d463e8c2f12cb74204b4a
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

反応ノート

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