Bromobenzyl Cyanide → N-(4-amino-5-phenyl-thiazol-2-yl)-acetamide

HRID 874162

反応式

HRID 874162 の反応式
Br[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:3]#[N:4].[C:11]([NH:14][C:15]([NH2:17])=[S:16])(=[O:13])[CH3:12]>C(O)C>[C:11]([NH:14][C:15]1[S:16][C:2]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[C:3]([NH2:4])[N:17]=1)(=[O:13])[CH3:12]

参加物

4

反応物 2

HCID 22044Bromobenzyl CyanideHCID 2723593Acetylthiourea

生成物 1

HCID 85841531N-(4-amino-5-phenyl-thiazol-2-yl)-acetamide収率 23.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

α-Bromophenylacetonitrile (1.08 g, 5.48 mmol) in ethanol (10 ml) was treated with N-acetylthiourea (649 mg, 5.49 mmol) at ambient temperature for 4 hr, and then heated to reflux for 3.5 hr. The cooled mixture was concentrated in vacuo and then partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded 2-(acetylamino)-4-amino-5-phenylthiazole (295 mg, 23%).

後処理

  1. temperatureheated
  2. temperatureto reflux for 3.5 hr
  3. concentrationThe cooled mixture was concentrated in vacuo
  4. custompartitioned between dichloromethane and saturated aqueous sodium bicarbonate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ac4089a78c634ae690e094c6205119d1
出典データセット
uspto-grants-2015_03
特許番号
US08980837B2

関連ノート

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