Ammonia → HCID 10085156, compound

HRID 382357Notes

Reaction equation

HRID 382357 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[C:18]([C:19](OC)=[O:20])[C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH3:23]>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([NH2:23])=[O:20])[C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 10661692HCID 10661692, compound

Product 1

HCID 10085156HCID 10085156, compound

Procedure

Following standard procedure C, methyl 2-(4′-nitrophenyl)-1-H-benzimidazole-4-carboxylate was dissolved in liquid ammonia and heated under constant volume in a pressure vessel. The product was purified by column chromatography from dichloromethane/methanol 99:1 and recrystallised from methanol. mp >310° C.; δH 7.48-7.56 (1H, t), 7.90-7.94 (1H, d), 8.00 (1H, s, NH), 8.00-8.04 (1H, d), 8.52-8.56 (2H, d, J=8.8), 8.60-8.64 (2H, d, J=8.8), 9.3-9.4 (1H, br s, NH), 13.8-14.0 (1H, br s, NH)

Workup

  1. temperatureheated under constant volume in a pressure vessel
  2. customThe product was purified by column chromatography from dichloromethane/methanol 99:1
  3. customrecrystallised from methanol

Sources & evidence

ORD record
ord-10f889f5271243f5b399b2d76efbf2f7
Source dataset
uspto-grants-2001_10
Patent number
US06310082B1

Reaction notes

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