Potassium Carbonate → 1-(p-Nitrobenzyl)-2-phenyl-4-chloro-5-formylimidazole

HRID 1706382Notes

Reaction equation

HRID 1706382 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.[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)([O-:17])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][N:8]2[C:9]([CH:13]=[O:14])=[C:10]([Cl:12])[N:11]=[C:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 178520008HCID 178520008, compound

Product 1

HCID 150993391-(p-Nitrobenzyl)-2-phenyl-4-chloro-5-formylimidazoleYield 79.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 50 ml of dimethylformamide, there were stirred 10.3 g of 2-phenyl-4-chloro-5-formylimidazole, 11.3 g of p-nitrobenzyl bromide and 5.2 g of anhydrous potassium carbonate at 110°-120° C. for 2 hours. The reaction mixture was poured in ice-water and the resulting precipitate was put on a column of 100 g silica gel, elution being carried out with chloroform. The first fraction was concentrated to dryness and recrystallized from ethanol. By the above procedure was obtained 13.6 g of 1-(p-nitrobenzyl)-2-phenyl-4-chloro-5-formylimidazole as colorless needles, m.p. 150°-152° C.

Workup

  1. washthe resulting precipitate was put on a column of 100 g silica gel, elution
  2. concentrationThe first fraction was concentrated to dryness
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6fff047956de46e381aecf1b45dd9ded
Source dataset
uspto-grants-1980_06
Patent number
US04207324

Reaction notes

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