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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1861962Generated: November 2, 2026

Ethyl Acetate → tert-butyl N-[4-(cyanomethyl)-2-methylphenyl]carbamate

https://huagongshe.com/reaction/1861962

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantSodium CyanideHCID 8929—
ReactantHCID 22981310HCID 22981310—
SolventDimethyl SulfoxideHCID 679—
Producttert-butyl N-[4-(cyanomethyl)-2-methylphenyl]carbamateHCID 5394373361.1%

Reaction Conditions

Temperature50 °C

Reaction Steps

The compound (155.1 mg) obtained in Example 519 was dissolved in dimethyl sulfoxide (5 ml). To the solution, sodium cyanide (127 mg) was added and the mixture was heated at 50° C. under stirring for 10 min. To the resulting reaction mixture, ethyl acetate was added and the organic layer was washed with water twice, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1) to give 77.7 mg of the titled compound (yield, 61%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06534546B1
Source datasetuspto-grants-2003_03
ORD IDord-0e2092eb16e741319a97bb91a82ba399
Source noteuspto-grants-2003_03