2-Propanone, 1-bromo-1-phenyl- → 2-(2-Chlorophenyl)-4-methyl-5-phenylthiazole

HRID 262127Notes

Reaction equation

HRID 262127 reaction equation
Br[CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](=O)[CH3:4].[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([NH2:17])=[S:16]>C(O)C>[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]1[S:16][C:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[C:3]([CH3:4])[N:17]=1

Participants

4

Reactant 2

HCID 908702-Propanone, 1-bromo-1-phenyl-HCID 27348242-Chlorothiobenzamide

Product 1

HCID 203449802-(2-Chlorophenyl)-4-methyl-5-phenylthiazoleYield 79.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Bromo-1-phenyl-2-propanone (10.6g, 0.050 mole), o-chlorothiobenzamide (8.8g, 0.051 mole), and ethanol (100 ml) are mixed and, after the initial exothermic reaction has subsided, heated under reflux for two hours. The ethanol is evaporated and the residue is treated with chloroform and aqueous sodium bicarbonate. The chloroform layer is separated and evaporated to leave a yellow oil which solidifies on standing. Recrystallization from acetonitrile yields 11.3g (79%) of 2-(2-chlorophenyl)-4-methyl-5-phenylthiazole, m.p. 63°-65° C.

Workup

  1. customafter the initial exothermic reaction
  2. temperatureheated
  3. temperatureunder reflux for two hours
  4. customThe ethanol is evaporated
  5. additionthe residue is treated with chloroform and aqueous sodium bicarbonate
  6. customThe chloroform layer is separated
  7. customevaporated
  8. customto leave a yellow oil which
  9. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-a2d9f3ac15984539875f6593735643a3
Source dataset
uspto-grants-1979_05
Patent number
US04153703

Reaction notes

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