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

HRID 874162

반응식

HRID 874162 반응식
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]

참가 물질

4

반응물 2

HCID 22044Bromobenzyl CyanideHCID 2723593Acetylthiourea

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ac4089a78c634ae690e094c6205119d1
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980837B2

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