Thionyl Chloride → 1-[1-(4-Chloro-3-methyl-phenyl)-1H-imidazol-4-yl-methyl]-4,5,6,7-tetrahydro-1H-benzoimidazole-, Hydrochloride

HRID 397866Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH2:13]O)[N:10]=[CH:9]2)=[CH:4][C:3]=1[CH3:15].S(Cl)(Cl)=O.[H-].[Na+].[N:22]1[C:26]2[CH2:27][CH2:28][CH2:29][CH2:30][C:25]=2[NH:24][CH:23]=1>>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH2:13][N:22]3[C:26]4[CH2:27][CH2:28][CH2:29][CH2:30][C:25]=4[N:24]=[CH:23]3)[N:10]=[CH:9]2)=[CH:4][C:3]=1[CH3:15]

Participants

Reactant 4

HCID 24386Thionyl Chloride

HCID 24758Sodium hydride

HCID 3042634,5,6,7-Tetrahydro-1H-benzimidazole

HCID 234450481-(4-Chloro-3-methylphenyl)-1H-imidazole-4-methanol

Product 1

HCID 1317240461-[1-(4-Chloro-3-methyl-phenyl)-1H-imidazol-4-yl-methyl]-4,5,6,7-tetrahydro-1H-benzoimidazole-, Hydrochloride

Procedure

[1-(4-Chloro-3-methyl-phenyl)-1H-imidazol-4-yl]-methanol was treated first with thionylchloride, then with the reaction mixture of sodium hydride and 4,5,6,7-tetrahydro-benzimidazole. After extractive workup and chromatography the title compound was obtained as the free base. It was converted into its white hydrochloride salt. Mp.>250° C. (MeOH/Et2O), MS: m/e=326 (M+).

Sources & evidence

ORD record: ord-cc5ad3c8fa5e49c0b6c1114a6e0e6dfa
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610723B2

Reaction notes

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