Hydroxylamine HCl → 5-Nitro-benzimidazole-2-carboxamide oxime

HRID 1250443Notes

Reaction equation

HRID 1250443 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[N:8]=[C:9]([C:11]#[N:12])[NH:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[Cl-].[OH:16][NH3+:17].C([O-])(=O)C.[Na+]>C(O)C.O>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[N:8]=[C:9]([C:11](=[N:17][OH:16])[NH2:12])[NH:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 217228915-nitro-1H-benzo[d]imidazole-2-carbonitrile

Product 1

HCID 1360030765-Nitro-benzimidazole-2-carboxamide oximeYield 68.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

2 g of 5-nitrobenzimidazole-2-carbonitrile (Lopyrev, V. A.; Larina, L. I.; Baumane, L. Kh.; Shibanova, E. F.; Gavar, R. A.; et al., Chem. Heterocycl. Compd. (Engl. Transl.), EN, 20, 9, 1984, 1021-1026, KGSSAQ, RU, 20, 9, 1984, 1246-1251) are dissolved in 60 ml of ethanol/water (5/1) and treated with 0.74 g of hydroxylammonium chloride and also 1.05 g of sodium acetate and refluxed for 2 h. The mixture is poured into ice water, and the brown precipitate is filtered off with suction and washed with water. 1.6 g of the title compound are obtained.

Workup

  1. temperaturerefluxed for 2 h
  2. filtrationthe brown precipitate is filtered off with suction
  3. washwashed with water

Sources & evidence

ORD record
ord-7066b624330a4a2a9c3c6069a6a6ae99
Source dataset
uspto-grants-2002_01
Patent number
US06339083B1

Reaction notes

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