Water → 1H-Benzimidazole-4-carbohydrazide

HRID 605891Notes

Reaction equation

HRID 605891 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, J=8.0 Hz), 7.34 (t, 1H, J=8.0 Hz), 4.68 (s, 2H).

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-a0d2fb2f67e44c0f9136e0a503442490
Source dataset
uspto-grants-2011_03
Patent number
US07915280B2

Reaction notes

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