Water → 1H-Benzimidazole-4-carbohydrazide

HRID 1767681Notes

Reaction equation

HRID 1767681 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-6a4dd83572c947db8f9a9740f2244af9
Source dataset
uspto-grants-2007_06
Patent number
US07235557B2

Reaction notes

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