Hydroxylamine → N'-hydroxy-3H-benzimidazole-5-carboximidamide

HRID 400716Notes

Reaction equation

HRID 400716 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH2:12][OH:13]>CCO>[OH:13][N:12]=[C:10]([C:8]1[CH:7]=[CH:6][C:5]2[NH:1][CH:2]=[N:3][C:4]=2[CH:9]=1)[NH2:11]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 178509527HCID 178509527, compound

Product 1

HCID 178513241N'-hydroxy-3H-benzimidazole-5-carboximidamideYield 93.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1H-benzimidazole-5-carbonitrile obtained in step 1 (1 g; 6.99 mmol) in EtOH (20 mL) was added hydroxylamine (50% in water, 2.10 mL; 34.93 mmol) and the mixture was stirred at RT for 36 hours. The solution was concentrated under vacuum to give the title compound as a light pink solid (1.15 g, 93%). 1H NMR (DMSO-d6): δ 12.52 (br s, 1H), 9.51 (s, 1H), 8.23 (s, 1H), 7.89 (br s, 1H), 7.56 (s, 2H), 5.80 (s, 2H).

Workup

  1. concentrationThe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-45500b74b35c4087b882fdac84bc987e
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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