Hydrochloric Acid → HCID 178441479, compound

HRID 1655475Notes

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][CH2:32][CH3:33])=[O:30])=[CH:26][CH:27]=[CH:28][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[N-:34]=[N+:35]=[N-:36].[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:36][N:35]=[N:34][N:24]=3)=[CH:15][CH:16]=2)[C:8]2[C:25]([C:29]([O:31][CH2:32][CH3:33])=[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 ethyl 2-butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole-7-carboxylate (0.21 g), sodium azide (1.3 g) and ammonium chloride (1.07 g) in DMF (8 ml) was stirred for 60 hours at 110-120° C. To the mixture was added water and the mixture was made acidic (pH 3-4) with 1N-HCl, followed by extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated to dryness. To the concentrate was added ether, and resulting crude crystals were collected by filtration, followed by recrystallization from ethanol to afford colorless crystals (0.95 mg, 41%), m.p. 138-139° C.

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water
customdried
concentrationconcentrated to dryness
additionTo the concentrate was added ether
customresulting crude crystals
filtrationwere collected by filtration
customfollowed by recrystallization from ethanol

Sources & evidence

ORD record: ord-1302293a5f7546c28212c82d389da743
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05250554

Reaction notes

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