p-Toluohydrazide → 4-Methyl-benzoic acid-(1-imino-ethyl)-hydrazide

HRID 1787848Notes

Reaction equation

HRID 1787848 reaction equation
[Na].Cl.C(O[C:6](=[NH:8])[CH3:7])C.[CH3:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([NH:16][NH2:17])=[O:15])=[CH:12][CH:11]=1>C(O)C>[NH:8]=[C:6]([N:16]([C:14](=[O:15])[C:13]1[CH:12]=[CH:11][C:10]([CH3:9])=[CH:19][CH:18]=1)[NH2:17])[CH3:7]

Participants

5

Reactant 3

HCID 77174p-ToluohydrazideHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 5360545Sodium

Product 1

HCID 684954674-Methyl-benzoic acid-(1-imino-ethyl)-hydrazideYield 15.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.65 g (72 mmol) of sodium are dissolved in 80 mL ethanol. 8.89 g (72 mmol) of ethylacetimidate hydrochloride in 160 mL ethanol are added at ambient temperature and the precipitated sodium chloride is filtered off. The filtrate is combined with 6.00 g (40 mmol) 4-methyl-benzoic acid hydrazide and stirred overnight. The reaction mixture is evaporated down and cooled. The precipitated solid is filtered off and washed with cold ethanol and diethyl ether (5.7 g of white solid). A further 1.2 g of solid are obtained from the filtrate after the removal of the solvent by distillation and recrystallisation from ethanol. Yield: 6.93 g (91%); mass spectroscopy [M+H]+=192.

Workup

  1. filtrationthe precipitated sodium chloride is filtered off
  2. customThe reaction mixture is evaporated down
  3. temperaturecooled
  4. filtrationThe precipitated solid is filtered off
  5. washwashed with cold ethanol and diethyl ether (5.7 g of white solid)

Sources & evidence

ORD record
ord-d01719cb473e41ad981816ef2ffe3e85
Source dataset
uspto-grants-2009_03
Patent number
US07511067B2

Reaction notes

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