Ethanol → Thiazole, 4-(4-chlorophenyl)-5-methyl-2-phenyl-

HRID 350709Notes

Reaction equation

HRID 350709 reaction equation
Br[CH:2]([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=O.[C:13]([NH2:21])(=[S:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(=O)C.[Na+].C(O)C>O>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:21]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:20][C:2]=2[CH3:12])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 683563ThiobenzamideHCID 37882192-Bromo-1-(4-chlorophenyl)propan-1-one

Product 1

HCID 8036414Thiazole, 4-(4-chlorophenyl)-5-methyl-2-phenyl-Yield 68.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-bromo-4′-chloropropiophenone (45.0 g), thiobenzamide (24.7 g), sodium acetate (14.8 g) and ethanol (400 mL) was stirred with heating under reflux for 3 hrs. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated to give 4-(4-chlorophenyl)-5-methyl-2-phenylthiazole (35.1 g, 68%) as crystals. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 90–91° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e8f752d4746b4f299475521265f288a2
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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