Acetohydrazide → N-Benzylethanehydrazonic acid

HRID 1514355Notes

Reaction equation

HRID 1514355 reaction equation
[C:1]([NH:4][NH2:5])(=[O:3])[CH3:2].Br[C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9]Br>C(O)C>[CH2:9]([NH:5][NH:4][C:1](=[O:3])[CH3:2])[C:8]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:7]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 769652-Bromobenzyl bromide

Product 1

HCID 250611N-Benzylethanehydrazonic acidYield 129.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Acetic hydrazide (1.78 g, 24 mmol) was dissolved in ethanol (20 mL) and cooled to 0° C. A solution of 2-bromobenzyl bromide (2 g, 8 mmol) in ethanol (10 mL) was added slowly and stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the crude product was purified by column chromatography with ethyl acetate-hexane as eluent to give acetic acid N′-benzyl-hydrazide (1.7 g, 87%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude product was purified by column chromatography with ethyl acetate-hexane as eluent

Sources & evidence

ORD record
ord-68b684eb13fd46ba936587dc2ea4d111
Source dataset
uspto-grants-2012_07
Patent number
US08222262B2

Reaction notes

Loading…