Benzyl Chloride → 2,2-Dimethyl-1,5-diphenyl-4-(1H-1,2,4-triazol-1-yl)pentan-3-one

HRID 1789070Notes

Reaction equation

HRID 1789070 reaction equation
[CH3:1][C:2]([CH3:18])([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3](=[O:10])[CH2:4][N:5]1[CH:9]=[N:8][CH:7]=[N:6]1.[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[K+]>O.CS(C)=O>[C:12]1([CH2:11][C:2]([CH3:18])([CH3:1])[C:3](=[O:10])[CH:4]([N:5]2[CH:9]=[N:8][CH:7]=[N:6]2)[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 14797Potassium HydroxideHCID 132100523,3-Dimethyl-4-phenyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

Product 1

HCID 132100532,2-Dimethyl-1,5-diphenyl-4-(1H-1,2,4-triazol-1-yl)pentan-3-oneYield 81.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

48.6 g (0.2 mol) of 3,3-dimethyl-4-phenyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 27.9 g (0.22 mol) of benzyl chloride and 12.3 g (0.22 mol) of potassium hydroxide in 15 ml of water are dissolved in 300 ml of dimethylsulphoxide. The reaction mixture is stirred for a further 8 hours at 50° C. and then poured onto water. The mixture is extracted with ethyl acetate. The organic phase is concentrated and the residue is purified by column chromatography (silica gel/ethyl acetate: cyclohexane =3:1). 54.5 g (81.8% of theory) of 1,5-bisphenyl-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-pentan-3-one of melting point 45°-50° C. are obtained.

Workup

  1. additionpoured onto water
  2. extractionThe mixture is extracted with ethyl acetate
  3. concentrationThe organic phase is concentrated
  4. customthe residue is purified by column chromatography (silica gel/ethyl acetate: cyclohexane =3:1)

Sources & evidence

ORD record
ord-6ff56abd36cd489b8cb4b6495cf0458f
Source dataset
uspto-grants-1987_08
Patent number
US04686291

Reaction notes

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