Ammonium Chloride → 2-(p-Tolyl)imidazole-5-methanol

HRID 277717

Reaction equation

HRID 277717 reaction equation
Cl.[CH3:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.[OH:12][CH:13](O)[C:14](=O)[CH3:15].[Cl-].[NH4+]>[OH-].[NH4+]>[CH3:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[NH:8][C:14]([CH2:13][OH:12])=[CH:15][N:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1227534-Methylbenzene-1-carboximidamide hydrochlorideHCID 131809821,1-Dihydroxypropan-2-one

Product 1

HCID 130112422-(p-Tolyl)imidazole-5-methanol

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4 g 4-methylbenzamidine hydrochloride in 60 mL ammonium hydroxide was treated with 4.0 g with dihydroxyacetone and 4.8 g ammonium chloride. The reaction mixture was heated to 90° C. for 4 hours in a sealed tube. On cooling to room temperature a the solid formed was collected by filtration to yield 3.0 g 2-(4-methylphenyl)-5-hydroxymethyl-imidazole which was converted according to the procedure described in Example VII to yield 2-(4-methylphenyl-4(5)-[(4-(2-pyrimidinyl)-piperazin-1-yl)-methyl]-imidazole (Compound 133), m.p. 178-180° C.

Workup

  1. temperatureOn cooling to room temperature a the solid
  2. customformed
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-eb9e6dfdad7f4a07895fb90217f1a43f
Source dataset
uspto-grants-2002_03
Patent number
US06358955B1

Linked notes

Loading…