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

HRID 1864769Notes

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.C1(C)C=CC=CC=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.[OH-:26].[Na+]>O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:9][CH2:10][CH:11]([OH:26])[CH2:12][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 94 °C

Procedure

To a solution of 56.7 g (0.26 mol) of 1-chloro-4-chlorophenyl-2-butanol (J. of Medicinal Chemistry, 1978. Vol. 21. No. 8. p. 842) in 200 ml of toluene 36.2 g (0.9 mol) of sodium hydroxide dissolved in 100 ml of water, 6.4 g (0.028 mol) of benzyltriethyammonium chloride and 35.2 g (0.51 mol) of imidazole (III) are added. The reaction mixture is heated at 93-95° C. for one hour then the temperature is returned to about 60° C., the phases are separated and to the organic layer water (100 ml) is added. The mixture is first stirred at 22-25° C. for 1 hour then at 0-5° C. for two hours. The crystals are separated by filtration, washed with water (2×35 ml) of 0-5° C. to yield 74 g of wet (1-[4-(4-chlorophenyl)-2-hydroxy-n-butyl]-imidazole) which is dried at maximum 50° C. in vacuo to give 61.6 g (95%) of the product. Recrystallization from ethyl acetate gives 52.4 g (85%) of dry product melting at 104-106° C.

Workup

customis returned to about 60° C.
customthe phases are separated and to the organic layer water (100 ml)
additionis added
waitat 0-5° C. for two hours
customThe crystals are separated by filtration
washwashed with water (2×35 ml) of 0-5° C.

Sources & evidence

ORD record: ord-138a9c2f2c3149689e00def8f868b291
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625935B2

Reaction notes

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