N-bromobutanimide → Ethyl 4-(bromomethyl)-2-phenyl-1,3-thiazole-5-carboxylate

HRID 642276

反応式

HRID 642276 の反応式
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:17])=[O:5])[CH3:2].[Br:18]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:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:17][Br:18])=[O:5])[CH3:2]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 2743970Ethyl 4-methyl-2-phenyl-1,3-thiazole-5-carboxylate

生成物 1

HCID 12736369Ethyl 4-(bromomethyl)-2-phenyl-1,3-thiazole-5-carboxylate収率 100.4%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 4-methyl-2-phenyl-thiazole-5-carboxylic acid ethyl ester (5.04 g, 0.02 mol), N-bromosuccinimide (3.8 g, 0.02 mol) and benzoyl peroxide (247 mg, 1 mmol) in carbon tetrachloride (60 mL) was refluxed for 17 h before it was cooled to room temperature and filtered. The filtrate was washed with water, saturated aqueous sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (6.55 g): 1H NMR (CDCl3, 200 MHz): δ=7.94 (m, 2H), 7.44 (m, 3H), 7.03 (m, 1H), 4.98 (s, 3H), 4.41 (q, J=7.0 Hz, 2H), 1.41 (t, J=7.0 Hz, 3H); MS: (+) m/z 326.0, 328.0 (M+1, 79Br/81Br).

後処理

  1. temperaturewas refluxed for 17 h before it
  2. filtrationfiltered
  3. washThe filtrate was washed with water, 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-024b848655bd49be8a2c73570b41338f
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

関連ノート

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