Phenacyl bromide → 4-Phenyl-2-(thien-2-yl)thiazole

HRID 414228

반응식

HRID 414228 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[S:8])[NH2:7].Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O>C(O)C.O>[C:13]1([C:11]2[N:7]=[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[S:8][CH:10]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 2

HCID 6259Phenacyl bromideHCID 7372372-Thiophenecarbothioamide

생성물 1

HCID 28102214-Phenyl-2-(thien-2-yl)thiazole수율 93.5%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a stirred solution of 2-thiophenethiocarboxamide (1.56 g, 0.0109 mole) in ethanol (50 mL) was added 2-bromoacetophenone (2.19 g, 0.0110 mole). After complete addition the mixture was heated at reflux for two hours, then was allowed to cool to room temperature and stir for approximately 18 hours. The solvent was removed from the reaction mixture by evaporation under reduced pressure, leaving an oil which solidified. This solid was suspended in water and extracted twice with methylene chloride. The extracts were combined, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 2.48 g of 4-phenyl-2-(thien-2-yl)thiazole as a solid, mp 51°-53° C.

후처리

  1. additionAfter complete addition the mixture
  2. temperaturewas heated
  3. temperatureat reflux for two hours
  4. customThe solvent was removed from the reaction mixture by evaporation under reduced pressure
  5. customleaving an oil which
  6. extractionextracted twice with methylene chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-e7d3a8d4bde348a2a637bf8b80c240c0
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04791124

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