Water → 2-(1,2,4-Triazol-1-yl)-3-phenyl-4'-chlorobutyrophenone

HRID 25962

Reaction equation

HRID 25962 reaction equation
[N:1]1([CH2:6][C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].[CH3:18][CH:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C)C=O>[N:1]1([CH:6]([CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:18])[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 12648(1-Chloroethyl)benzeneHCID 24758Sodium hydrideHCID 7164721-(4-Chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one

Product 1

HCID 213260662-(1,2,4-Triazol-1-yl)-3-phenyl-4'-chlorobutyrophenone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(1,2,4-Triazol-1-yl)-4'-chloroacetophenone (0.01 mol) was dissolved in dimethylformamide (5.0 ml) at room temperature and treated with sodium hydride (0.01 mol). When the reaction was complete (3 hours), the mixture was cooled to 0° and α-methylbenzyl chloride (0.01 mol) was added dropwise with stirring. After stirring at room temperature for 20 hours, the mixture was poured into water and the product filtered off. Recrystallisation from chloroform/petroleum ether (60°-80°) gave the title compound as a colourless crystalline solid, m.p. 163°-5°.

Workup

  1. custom(3 hours)
  2. temperaturethe mixture was cooled to 0°
  3. stirringAfter stirring at room temperature for 20 hours
  4. filtrationthe product filtered off
  5. customRecrystallisation from chloroform/petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-44df194a82344c0692ea99da4c9c4b5d
Source dataset
uspto-grants-1979_04
Patent number
US04147793

Linked notes

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