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

HRID 2407709ノート

反応式

HRID 2407709 の反応式
[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]

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 100.1%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-28f09c425f3d43fabfdcea9eb508e1f1
出典データセット
uspto-grants-2014_08
特許番号
US08809538B2

反応ノート

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