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

HRID 642276

반응식

HRID 642276 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-024b848655bd49be8a2c73570b41338f
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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