Acetonitrile → 1-(4-methylphenyl)-2-(1h-1,2,4-triazol-1-yl)ethanone

HRID 1729271Notes

Reaction equation

HRID 1729271 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=[O:4].N1C=[CH:15][N:14]=[N:13]1.[Na].[C:18](#[N:20])C>>[N:14]1([CH2:2][C:3]([C:5]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=2)=[O:4])[CH:15]=[N:20][CH:18]=[N:13]1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 692722-Bromo-4'-methylacetophenoneHCID 178507080HCID 178507080, compound

Product 1

HCID 7393711-(4-methylphenyl)-2-(1h-1,2,4-triazol-1-yl)ethanone

Procedure

2-Bromo-4'-methylacetophenone (12.78 g; 0.06 mole), sodium triazole (5.46 g; 0.06 mole) in dry acetonitrile solution (100 ml) were stirred at 20° C. for 5 hours. The solvent was evaporated and the residue purified by chromatography using silica gel/chloroform to give 2-(1,2,4-triazol-1- yl)-4'-methylacetophenone as a white solid (mp 118.4° C.). The latter compound (3.0 g; 0.015 mole) together with sodium acetate (1.23 g; 0.015 mole) and acetic acid (30 ml), was stirred at 40° C. during the addition of bromine (2.38 g; 0.015 mole) in acetic acid (2 ml). The mixture was stirred for a further 30 minutes and poured into chloroform (50 ml) and washed with water and sodium bicarbonate solution. The chloroform layer was separated, dried (MgSO4) and evaporated to give crude 2-bromo-2-(1,2,4-triazol-1-yl)-4'-methylacetophenone.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-64e0abc5f9724e07ac5ce3349688875d
Source dataset
uspto-grants-1994_07
Patent number
US05332753

Reaction notes

Loading…