Water → 1-(4-Chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-3-pentanone

HRID 483115Notes

Reaction equation

HRID 483115 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:14])([C:6](=[O:13])[CH2:7][N:8]1[CH:12]=[N:11][CH:10]=[N:9]1)[CH3:5].[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.O>CN(C)C=O>[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][CH:7]([N:8]2[CH:12]=[N:11][CH:10]=[N:9]2)[C:6](=[O:13])[C:4]([CH3:14])([CH3:3])[CH3:5])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 1008773,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone

Product 1

HCID 129255611-(4-Chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-3-pentanoneYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

7.5 g (0.25 mol) of sodium hydride (80% strength suspension in oil) are slowly introduced, at 10° C., into a solution of 50.1 g (0.3 mol) of 2,2-dimethyl-4-(1,2,4-triazol-1-yl)-butan-3-one in 150 ml of absolute N,N-dimethylformamide, and the mixture is stirred at 20° C. until the evolution of gas has ended. A solution of 62 g (0.3 mol) of 4-chlorobenzyl bromide in 50 ml of N,N-dimethylformamide is then added dropwise, while stirring. After 5 hours, the reaction mixture is stirred into 900 ml of water, and the solid product which separates out is filtered off and recrystallized from 175 ml of ethanol. 55.6 g (76.3% of theory) of 5-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-pentan-3-one are obtained in the form of colorless crystals of melting point 124° C.

Workup

  1. stirringwhile stirring
  2. filtrationthe solid product which separates out is filtered off
  3. customrecrystallized from 175 ml of ethanol

Sources & evidence

ORD record
ord-31dfd0039f9342e1a30785bd03b8b64c
Source dataset
uspto-grants-1986_03
Patent number
US04578396

Reaction notes

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