Water → 1H-Benzimidazole-4-carbohydrazide

HRID 1445287Notes

Reaction equation

HRID 1445287 reaction equation
C[O:2][C:3]([C:5]1[C:10]2[N:11]=[CH:12][NH:13][C:9]=2[CH:8]=[CH:7][CH:6]=1)=O.O.[NH2:15][NH2:16].O>CCO>[N:11]1[C:10]2[C:5]([C:3]([NH:15][NH2:16])=[O:2])=[CH:6][CH:7]=[CH:8][C:9]=2[NH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 14970852Methyl 1H-benzimidazole-4-carboxylate

Product 1

HCID 450778831H-Benzimidazole-4-carbohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzimidazole ester 3 (1.65 g, 9.36 mmol), hydrazine monohydrate (10 mL), and water (3 mL) were refluxed in EtOH (60 mL) for 24 hs. Reaction mixture was cooled to room temperature and solid formed was filtered, washed with EtOH and dried to give 1.13 g (68%) of pure 4: 1H NMR (DMSO-d6) δ 12.31 (br.s, 1H), 10.59 (s, 1H), 8.44 (s, 1H), 7.86 (d, 1H, J=6.5 Hz), 7.76 (d, 1H, J8.0 Hz), 7.34 (t, 1H, J=8.0 Hz), 4.68 (s, 1H).

Workup

  1. customReaction mixture
  2. customsolid formed
  3. filtrationwas filtered
  4. washwashed with EtOH
  5. customdried
  6. customto give 1.13 g (68%) of pure 4

Sources & evidence

ORD record
ord-7d7a7204aae249b09a48082cdcbd18cb
Source dataset
uspto-grants-2010_02
Patent number
USRE041150E1

Reaction notes

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