Sodium Azide → 1-(Azidomethyl)cyclopropanecarbonitrile

HRID 408860Notes

Reaction equation

HRID 408860 reaction equation
CS(O[CH2:6][C:7]1([C:10]#[N:11])[CH2:9][CH2:8]1)(=O)=O.[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C)C=O.O.C(OCC)(=O)C.CCOCC>[N:12]([CH2:6][C:7]1([C:10]#[N:11])[CH2:9][CH2:8]1)=[N+:13]=[N-:14]

Participants

7

Reactant 2

HCID 33557Sodium AzideHCID 54220629(1-Cyanocyclopropyl)methyl methanesulfonate

Product 1

HCID 866351321-(Azidomethyl)cyclopropanecarbonitrileYield 68.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

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-dimethyl 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.

Workup

  1. temperatureto cool
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto give an oil
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5597d936b6ae4680a161d3e6251e8fdc
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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