Water → HCID 15099359, compound

HRID 223512Notes

Reaction equation

HRID 223512 reaction equation
[C:1]1([C:7]2[NH:8][C:9]([CH2:13][OH:14])=[C:10]([Cl:12])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][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)C=O>[C:1]1([C:7]2[N:8]([CH2:15][C:16]3[CH:23]=[CH:22][C:19]([CH3:20])=[CH:18][CH:17]=3)[C:9]([CH2:13][OH:14])=[C:10]([Cl:12])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7721p-Xylyl bromideHCID 11430Potassium CarbonateHCID 15088597HCID 15088597, compound

Product 1

HCID 15099359HCID 15099359, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of 2-phenyl-4-chloro-5-hydroxymethylimidazole, together with 0.7 ml of p-methylbenzyl bromide and 3 g of potassium carbonate, was stirred in 10 ml of dimethylformamide at 30° C. for 2 days. The reaction solution was poured into 100 ml of water, and the precipitate deposited was chromatographed on a column of 30 g of silica gel, followed by eluting with chloroform. The initially eluted fraction was collected, and recrystallization from aqueous methanol yielded 0.5 g of 2-phenyl-4-chloro-5-hydroxymethyl-1-(4-methylbenzyl)imidazole as colorless, needle-formed crystals, m.p. 173°-175° C.

Workup

  1. customthe precipitate deposited was chromatographed on a column of 30 g of silica gel
  2. washby eluting with chloroform
  3. customThe initially eluted fraction was collected
  4. customrecrystallization from aqueous methanol

Sources & evidence

ORD record
ord-d8d2554a8ca646f489b03b5b41151f63
Source dataset
uspto-grants-1982_10
Patent number
US04355040

Reaction notes

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