Hydrazinecarboxaldehyde → (N-Formylhydrazino)-imino acetic acid ethyl ester

Reaction equation

[CH3:1][CH2:2][O:3][C:4]([C:6]([NH2:8])=S)=[O:5].[CH:9]([NH:11][NH2:12])=[O:10]>>[CH2:2]([O:3][C:4](=[O:5])[C:6]([N:11]([CH:9]=[O:10])[NH2:12])=[NH:8])[CH3:1]

Participants

Reactant 2

HCID 12229Hydrazinecarboxaldehyde

HCID 2733398Ethyl thiooxamate

Product 1

HCID 86590617(N-Formylhydrazino)-imino acetic acid ethyl esterYield 76.3%

Conditions

Temperature: 65 °C

Procedure

A mixture of ethyl thioxamate (10.55 g, 79.2 mmol) and formylhydrazine (5.00 g, 83.2 mmol) was heated at 65° C. for 30 minutes and stirred in accordance with a method described in Collect. Czech Chem. Commun., 1984, 49, p 2492. After cooling, the precipitated crystal was collected by filteration and washed with ethanol to give (N-formylhydrazino)-imino acetic acid ethyl ester (9.62 g). Yield: 76%.

Workup

customin Collect
temperatureAfter cooling
customthe precipitated crystal was collected by filteration
washwashed with ethanol

Sources & evidence

ORD record: ord-a62cf4c9ffc84cf08a93f17d6e865c73
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098201B2

Reaction notes

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