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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1878333Generated: November 2, 2026

Sodium Azide → 1-(Azidomethyl)cyclopropanecarbonitrile

https://huagongshe.com/reaction/1878333

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium AzideHCID 33557—
Reactant(1-Cyanocyclopropyl)methyl methanesulfonateHCID 54220629—
SolventFormamideHCID 713—
SolventWaterHCID 962—
SolventDiethyl EtherHCID 3283—
SolventEthyl AcetateHCID 8857—
Product1-(Azidomethyl)cyclopropanecarbonitrileHCID 8663513268.5%

Reaction Conditions

Temperature120 °C

Reaction Steps

A stirred mixture of (1-cyanocyclopropyl)methyl methanesulfonate (21.52 mmol, 3.77 g) and sodium azide (43.0 mmol, 2.80 g) in N,N-diemethyl formamide (40 mL) was heated to 120° C. for ˜18 hours. The mixture was allowed to cool and was diluted with water and ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure to give an oil. This oil was taken up in ether and washed with water, dried and concentrated under reduced pressure to give the intermediate 1-(azidomethyl)cyclopropanecarbonitrile (1.8 g) as an oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08314091B2
Source datasetuspto-grants-2012_11
ORD IDord-4edaa6fcfe994d5b84eba45e5b8b845d
Source noteuspto-grants-2012_11