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

HRID 414228

Reaction equation

HRID 414228 reaction equation
[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

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 7372372-Thiophenecarbothioamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e7d3a8d4bde348a2a637bf8b80c240c0
Source dataset
uspto-grants-1988_12
Patent number
US04791124

Linked notes

Loading…