Ammonia → HCID 10729476, compound

HRID 382360Notes

Reaction equation

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

Participants

Reactant 2

HCID 222Ammonia

HCID 10592295HCID 10592295, compound

Product 1

HCID 10729476HCID 10729476, compound

Procedure

Following standard procedure C, the acetate salt of methyl 2-(4′-aminophenyl)-1-H-benzimidazole-4-carboxylate (113 mg, 0.346 mmol) was treated with liquid ammonia under pressure for 24 hours. The pure title compound was isolated with column chromatography of the crude material using dichloromethane/methanol 90:10 (21.4 mg, 25%) mp 237-240° C.; δH 5.90 (2H, s, NH2), 6.79-6.83 (2H, d, J=8.3), 7.31-7.39 (1H, t), 7.71-7.75 (1H, d), 7.84 (1H, s, NH), 7.88-7.92 (1H, d), 8.00-8.04 (2H, d, J=8.3), 9.5-9.6 (1H, br s, NH), 13.0 (1H, br s, NH).

Sources & evidence

ORD record: ord-ae2f149afbc04f609da536be2df2c301
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310082B1

Reaction notes

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