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

HRID 2407709

반응식

HRID 2407709 반응식
[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:18][CH2:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

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 100.1%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

Ethyl 4-methyl-2-phenylthiazole-5-carboxylate (5.00 g), N-bromosuccinimide (3.78 g) and benzoyl peroxide (0.49 g) were suspended in carbon tetrachloride (50 mL) and heated at reflux overnight. The reaction mixture was cooled to room temperature and partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The combined organics were dried over magnesium sulfate and concentrated under reduced pressure to afford the crude title compound (6.60 g), which was used without further purification possessing the following physical data.

후처리

  1. temperatureheated
  2. temperatureat reflux overnight
  3. custompartitioned between dichloromethane and saturated aqueous sodium bicarbonate
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-28f09c425f3d43fabfdcea9eb508e1f1
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809538B2

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