2-Bromo-4'-methylacetophenone → 2-(4'-Fluorophenyl)-4-(p-tolyl)thiazole

HRID 651386Notes

Reaction equation

HRID 651386 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)=O>CCO>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:7][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 692722-Bromo-4'-methylacetophenoneHCID 7372234-Fluorothiobenzamide

Product 1

HCID 113347062-(4'-Fluorophenyl)-4-(p-tolyl)thiazoleYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the crude product of 4-fluorothiobenzamide (2.0 g, 12.9 mmol) in EtOH (30 ml) is added 2-bromo-4′methylacetophenone (2.75 g, 12.9 mmol). The mixture is heated to reflux for 24 hours. The course of the reaction is followed by thin layer chromatography. Upon completion of the reaction the solution is cooled to room temperature and the white precipitate filtered and dried under vacuum to yield 2- (4′-fluorophenyl)-4- (p-tolyl) thiazole (1.54 g, 54%). 1H NMR (DMSOd6): δ 2.35 (s, 1H), 7.28 (d, 2H), 7.38 (t, 2H), 7.94 (d, 2H), 8.08 (dd, 2H), 8.11 (s, 1H).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 24 hours
  3. customUpon completion of the reaction the solution
  4. filtrationthe white precipitate filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7fb5b984cece48ec803bc974633dda1e
Source dataset
uspto-grants-2001_08
Patent number
US06281217B1

Reaction notes

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