Benzyl Chloride → 1-Benzyl-2-phenyl-4-chloro-5-formylimidazole

HRID 1706381Notes

Reaction equation

HRID 1706381 reaction equation
[C:1]1([C:7]2[NH:8][C:9]([CH:13]=[O:14])=[C:10]([Cl:12])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:15]([N:8]1[C:9]([CH:13]=[O:14])=[C:10]([Cl:12])[N:11]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 178520008HCID 178520008, compound

Product 1

HCID 110338001-Benzyl-2-phenyl-4-chloro-5-formylimidazoleYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 150 ml of dimethylformamide, there were stirred 206.5 g of 2-phenyl-4-chloro-5-formylimidazole, 133 g of benzyl chloride and 103.5 g of anhydrous potassium carbonate at 110°-120° C. for an hour. The reaction mixture was poured in ice-water and the resulting precipitate was recovered by filtration and recrystallized from acetonitrile twice. By the above procedure was obtained 143 g of 1-benzyl-2-phenyl-4-chloro-5-formylimidazole as colorless needles, m.p. 117°-118° C.

Workup

  1. filtrationthe resulting precipitate was recovered by filtration
  2. customrecrystallized from acetonitrile twice

Sources & evidence

ORD record
ord-6bbe2ffd30ac4cd099fc9e8fcb5403b4
Source dataset
uspto-grants-1980_06
Patent number
US04207324

Reaction notes

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