4-(Bromoacetyl)pyridine hydrobromide → 1,1-Difluoro-1-phenyl-[4-(4-pyridyl)-2-thiazolyl]methane

HRID 4348

Reaction equation

HRID 4348 reaction equation
[F:1][C:2]([F:12])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([NH2:5])=[S:4].Br.Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)=O>C(O)C>[F:12][C:2]([C:3]1[S:4][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[N:5]=1)([F:1])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 27762394-(Bromoacetyl)pyridine hydrobromideHCID 140969602,2-Difluoro-2-phenylethanethioamide

Product 1

HCID 140969611,1-Difluoro-1-phenyl-[4-(4-pyridyl)-2-thiazolyl]methaneYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,2-difluoro-2-phenylthioacetamide (1.57 g, 0.0092 mol) in 95% ethanol (20 mL) was added α-bromo-4-acetylpyridine hydrobromide (3.20 g, 0.012 mol) and the mixture warmed on a steam bath for thirty minutes. The product was isolated in the usual way and recrystallized from ethyl acetate/hexane to afford 1,1-difluoro-1-phenyl-[4-(4-pyridyl)-2-thiazolyl]methane (1.27 g, 48%). mp. 54.5°-55.5° C.

Workup

  1. temperaturethe mixture warmed on a steam bath for thirty minutes
  2. customThe product was isolated in the usual way
  3. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ee8a5d8d7a7843959078967aa73d7741
Source dataset
uspto-grants-1988_02
Patent number
US04725606

Linked notes

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