Ammonia → HCID 1511, compound

HRID 382359Notes

Reaction equation

[NH3:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([O:21]C)=O)[C:12]=3[N:11]=2)[CH:7]=[CH:8][CH:9]=1>>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([NH2:1])=[O:21])[C:12]=3[N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

Reactant 2

HCID 222Ammonia

HCID 10569296HCID 10569296, compound

Product 1

HCID 1511HCID 1511, compoundYield 46%

Procedure

Following standard procedure C, a liquid ammonia solution of methyl 2-(3′-methoxyphenyl)-1-H-benzimidazole-4-carboxylate (203 mg, 0.596 mmol) was heated under constant volume. The solid residue was recrystallised from methanol to give the pure product (73.5 mg, 46%). mp 223-225° C.; Found C 67.52 H 4.91 N 15.62 C15H13N3O2 Requires C 67.42 H 4.87 N 15.73; vmax(cm−1) 3408.59, 3388.94, 3168.65, 1662.05, 1625.86, 1603.39; δH 3.99 (3H, s, OCH3), 7.22-7.27 (1H, d),7.43-7.51 (1H, t), 7.58-7.66 (1H, t), 7.85-8.01 (5H, m), 9.4-9.5 (1H, br s), 13.5 (1H, br s); m/z (EI) 267 (M+), 250.

Workup

customThe solid residue was recrystallised from methanol

Sources & evidence

ORD record: ord-39ae159c3c75483abb8649fd6b489006
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310082B1

Reaction notes

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