Hydrazine hydrate (1:1) → HCID 178426647, compound

HRID 2381855Notes

Reaction equation

HRID 2381855 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13]([C:17]#[N:18])=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:20][NH2:21]>C(O)C>[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13]([C:17]([NH:20][NH2:21])=[NH:18])=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68494206HCID 68494206, compound

Product 1

HCID 178426647HCID 178426647, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-benzyl-5-cyano-3-methylthiophene-2-carboxamide (0.80 g, 3.12 mmol) and hydrazine monohydrate (8.00 mL, 164.9 mmol) in ethanol was stirred at reflux for 18 h. The reaction mixture was allowed to cool to ambient temperature, and concentrated in vacuo. The residue was triturated with ethyl acetate to afford N-benzyl-5-(hydrazinyl(imino)methyl)-3-methylthiophene-2-carboxamide as a light yellow solid (0.65 g, 72%): MS (ES+) m/z 289.2 (M+1).

Workup

  1. temperatureat reflux for 18 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-dcdf6a21304744d4b630b6911eabd329
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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