Hydrochloric Acid → HCID 178441468, compound

HRID 653715Notes

Reaction equation

[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:13][CH:12]=2)[C:8]2[C:25]([C:29]([O:31]C)=[O:30])=[CH:26][CH:27]=[CH:28][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[N-:33]=[N+:34]=[N-:35].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C.O>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:24][N:35]=[N:34][N:33]=3)=[CH:15][CH:16]=2)[C:8]2[C:25]([C:29]([OH:31])=[O:30])=[CH:26][CH:27]=[CH:28][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of methyl 2-butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole-7-carboxylate (3.2 g), sodium azide (7.4 g) and ammonium chloride (6.1 g) in DMF (30 ml) was stirred for 4 days at 115° C. To the reaction mixture was added water, which was adjusted to pH 3-4 with 1N-HCl. Resulting crude crystals (1) were purified by column chromatography on silica gel. The crystals thus obtained were recrystallized from ethyl acetate - methanol to afford colorless prisms (2.27 g, 63%), m.p. 168°-169° C.

Workup

customResulting crude crystals (1)
customwere purified by column chromatography on silica gel
customThe crystals thus obtained
customwere recrystallized from ethyl acetate - methanol

Sources & evidence

ORD record: ord-4f060d0d552e4001971f8faf43e74191
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05128356

Reaction notes

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