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Water → 3-(4-Bromobenzyl)-5-chloro-2-phenyl-3H-imidazole-4-carbaldehyde

HRID 1019251
Notes
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Reaction equation

HRID 1019251 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:6]=1[CH:7]=[O:8].[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:5]2[C:6]([CH:7]=[O:8])=[C:2]([Cl:1])[N:3]=[C:4]2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:18][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 178520008HCID 178520008, compound

Product 1

HCID 109157723-(4-Bromobenzyl)-5-chloro-2-phenyl-3H-imidazole-4-carbaldehydeYield 71.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

3.0 g of 4-chloro-5-formyl-2-phenylimidazole (Chem. Pharm. Bull. 1976, 24(5), 960), 7.0 g of 4-bromobenzyl bromide and 11.7 g of K2CO3 are stirred at RT for 20 h in 200 ml of DMF. The reaction mixture is then poured onto 500 ml of water, and the precipitate is filtered off with suction and chromatographed on silica gel using DIP. 3.9 g of an amorphous foam are obtained.

Workup

  1. filtrationthe precipitate is filtered off with suction
  2. customchromatographed on silica gel using DIP

Sources & evidence

ORD record
ord-e69139195873471f8cbfb4b28e5fc809
Source dataset
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06486189B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes