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

HRID 2049274Notes

Reaction equation

HRID 2049274 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 (10.6 g, 0.050 mole), o-chlorothiobenzamide (8.8 g, 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 11.3 g (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-6c5df390d09c4601bfba77809ba65231
Source dataset
uspto-grants-1980_04
Patent number
US04197306

Reaction notes

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