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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 351824Generated: October 25, 2026

Methylhydrazine → 3-cyclopropyl-[1,2,4]oxadiazol-5-ylmethyl-N,N-dimethyl-formamidine

https://huagongshe.com/reaction/351824

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethylhydrazineHCID 6061—
ReactantN-PhthaloylglycineHCID 20825—
ReactantN'-HydroxycyclopropanecarboximidamideHCID 2794666—
Reactant4-(Aminomethyl)-3-cyclopropyl-1,2,4-oxadiazoleHCID 22713490—
ReactantN-[(3-cyclopropyl-1,2,4-oxadiazol-5-yl)methyl]phthalimideHCID 22713498—
Solvent1,2-DichloroethaneHCID 11—
SolventDimethylformamideHCID 6228—
Solvent1,1'-CarbonyldiimidazoleHCID 68263—
Product3-cyclopropyl-[1,2,4]oxadiazol-5-ylmethyl-N,N-dimethyl-formamidineHCID 86585599—

Reaction Conditions

Temperature130 °C

Reaction Steps

Scheme 3 describes the preparation of known starting materials. The processes for preparation of these compounds are also known or may be carried out in analogous manner to known methods. For example, N-[(3-cyclopropyl-1,2,4-oxadiazol-5-yl)methyl]phthalimide is prepared by reaction of N-phthaloylglycine in DMF and 1,1′carbonyldiimidazole, and followed by the addition of cyclopropanecarboxamidoxime. The obtained N-[(3-cyclopropyl-1,2,4-oxadiazol-5-yl)methyl]phthalimide is then dissolved in 1,2-dichloroethane and N-methylhydrazine is added. The obtained 4-(aminomethyl)-3-cyclopropyl-1,2,4-oxadiazole is then treated with N,N-dimethylformaldehyde diethyl acetal and heated at about 130° C. and the desired starting material (E/Z)-N′-(3-cyclopropyl-[1,2,4]oxadiazol-5-ylmethyl-N,N-dimethyl-formamidine is obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06743789B2
Source datasetuspto-grants-2004_06
ORD IDord-72e9f2e9c5ca4a129d217bbf2e0400c1
Source noteuspto-grants-2004_06