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

HRID 29797Notes

Reaction equation

HRID 29797 reaction equation
[Na].Cl.[C:3](=[NH:8])(OCC)[CH3:4].[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:3]([N:16]([C:14](=[O:15])[C:13]1[CH:12]=[CH:11][C:10]([CH3:9])=[CH:19][CH:18]=1)[NH2:17])[CH3:4]

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) sodium are dissolved in 80 mL ethanol. 8.89 g (72 mmol) ethyl acetimidate 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 white solid). A further 1.2 g solid are obtained from the filtrate after distillation of the solvents and recrystallisation from ethanol.

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 white solid)

Sources & evidence

ORD record
ord-7072e1c97cbd4655b956b63c85fe56c9
Source dataset
uspto-grants-2008_09
Patent number
US07423036B2

Reaction notes

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