Dimethylformamide → 1-(Cyanomethyl)-3-methylenecyclobutanecarbonitrile

HRID 1692928Notes

Reaction equation

HRID 1692928 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-b506813bfd04458a87d6207edec7029d
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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