Dimethylformamide → 1-(Cyanomethyl)-3-methylenecyclobutanecarbonitrile

HRID 1966154Notes

Reaction equation

HRID 1966154 reaction equation
CS(O[CH2:6][C:7]1([C:12]#[N:13])[CH2:10][C:9](=[CH2:11])[CH2:8]1)(=O)=O.[C-]#N.[K+].[CH3:17][N:18](C)C=O>O>[C:17]([CH2:6][C:7]1([C:12]#[N:13])[CH2:10][C:9](=[CH2:11])[CH2:8]1)#[N:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 86634345(1-Cyano-3-methylenecyclobutyl)methyl methanesulfonate

Product 1

HCID 668243831-(Cyanomethyl)-3-methylenecyclobutanecarbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of (1-cyano-3-methylenecyclobutyl)methyl methanesulfonate (0.41 g, 0.0020 mol) and potassium cyanide (0.66 g, 0.010 mol) in N,N-dimethylformamide (5 mL, 0.06 mol) was heated at 65° C. overnight. After diluting with water, the resulting mixture was extracted with EtOAc. The combined organic layers were washed with water, brine, dried and evaporated to dry. The residue was used directly in next step.

Workup

  1. extractionthe resulting mixture was extracted with EtOAc
  2. washThe combined organic layers were washed with water, brine
  3. customdried
  4. customevaporated
  5. customto dry

Sources & evidence

ORD record
ord-39663aa97586452ca0f4c81c898b239e
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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