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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1595206Generated: October 26, 2026

Trimethyl orthoacetate → Methyl N-(5-cyanoimidazol-4-yl)acetimidate

https://huagongshe.com/reaction/1595206

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrimethyl orthoacetateHCID 15050—
Reactant5-amino-1H-imidazole-4-carbonitrileHCID 78777—
SolventDimethylformamideHCID 6228—
ProductMethyl N-(5-cyanoimidazol-4-yl)acetimidateHCID 67550327—

Reaction Conditions

Temperature90 °C

Reaction Steps

5 g of 4-amino-5-cyanoimidazole was suspended in 10 mL of DMF and 10 mL of trimethyl orthoacetate was added, followed by stirring at 90° C. for 30 minutes. The reaction solution was concentrated under reduced pressure and the residue was dilute with ethyl acetate, and then 4.2 g of desired compound deposited as a crystal was collected by filtration. The solution was concentrated and the residue was purified by silica gel column chromatograpy (eluent: ethyl acetate) and then recrystallized from ethyl acetate-n-hexane to obtain 2.9 g of a desired compound as a crystal.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06288070B1
Source datasetuspto-grants-2001_09
ORD IDord-02d1fcf416d447a689f103c7f65d514e
Source noteuspto-grants-2001_09