Imidazole → 4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol

HRID 1864767Notes

Reaction equation

HRID 1864767 reaction equation
Cl[C:2]1([CH2:9][CH:10](O)[CH2:11][CH3:12])[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH2:3]1.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.[OH-:19].[Na+]>C1(C)C=CC=CC=1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:9][CH2:10][CH:11]([OH:19])[CH2:12][N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 14798Sodium HydroxideHCID 68824656HCID 68824656, compound

Product 1

HCID 109559944-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

We have surprisingly found that when the starting material 1-chloro-4-chlorophenyl-2-butanol (II) is reacted with the imidazole (III) in a mixture of toluene and aqueous sodium hydroxide solution in the presence of a phase transfer catalyst, the (1-[4-(4-chlorophenyl)-2-hydroxy-n-butyl]-imidazole) (IV) key intermediate is obtained with short reaction time and excellent yield (95%).

Sources & evidence

ORD record
ord-f060eda6eaca4d9fb933ae1d37585ad5
Source dataset
uspto-grants-2009_12
Patent number
US07625935B2

Reaction notes

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