Ammonia → HCID 10730177, compound

HRID 382356Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([C:18](OC)=[O:19])[C:11]=3[N:10]=2)=[CH:5][CH:4]=1)#[N:2].[NH3:22]>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([NH2:22])=[O:19])[C:11]=3[N:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

Reactant 2

HCID 222Ammonia

HCID 10778884HCID 10778884, compound

Product 1

HCID 10730177HCID 10730177, compound

Procedure

Following standard procedure C, methyl 2-(4′-cyanophenyl)-1-H-benzimidazole-4-carboxylate (169.5 mg, 0.612 mmol) was treated with ammonia under pressure. The crude product was recrystallised from boiling methanol to yield the title compound pure as white crystals. (116.5 mg, 73%) mp >310° C.; Found C 67.81 H 3.89 N 20.87, C15H10N4O.0.2 MeOH Requires C 67.95 H 4.05 N 20.85; vmax(cm−1) 3332.27, 3274.86, 3177.98, 2230.85, 1658.54, 1608.10; δH 7.45-7.49 (1H, t); 7.87-7.91 (1H, d), 7.91 (1H, br s), 7.98-8.02 (1H, d); 8.13-8.17 (2H, d, J=8.3), 8.50-8.54 (2H, d, J=8.3), 9.2-9.4 (1H, br s), 13.6-13.8 (1H, br 8); m/z (EI) 262 (M+), 245, 217, 102.

Workup

customThe crude product was recrystallised

Sources & evidence

ORD record: ord-e6b492db7aba47eebaf0eed0c210b337
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310082B1

Reaction notes

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