ChemicalBook CAS DataBase List Cyclobutanecarbonitrile

Cyclobutanecarbonitrile synthesis

8synthesis methods

Product Name:Cyclobutanecarbonitrile
CAS Number:4426-11-3
Molecular formula:C5H7N
Molecular Weight:81.12

1189-71-5
340 suppliers
$18.00/5g

3721-95-7 Synthesis

3721-95-7
408 suppliers
$7.00/5g

4426-11-3
117 suppliers
$25.00/1g

Yield:4426-11-3 66.5%

Reaction Conditions:

in dichloromethane;N,N-dimethyl-formamide

Steps:

27.a a
a Cyclobutanecarbonitrile A solution of 80 g (799 mmoles) of cyclobutanecarboxylic acid in 250 ml of dichloromethane is refluxed. 115.6 g (819 mmoles) of chlorosulfonylisocyanate are poured slowly dropwise. Reflux is continued one hour after the end of the addition, until complete evolution of CO₂. The reaction mixture is then cooled to 10° C. During 15 min., 119.6 g (1638 mmoles) of N,N-dimethylformamide are poured dropwise therein, before allowing stirring 1/4 hour at room temperature. Then, the mixture is poured over ice-water, before extracting it with dichloromethane. The organic phase washed with water, is dried over Na₂ SO₄, and concentrated under vacuum. The distillation of the residue gives 43.5 g (yield=66.5%) of a colorless liquid. b.p.₁₅ =50° C. I.R. (film): ν (C N)=2250 cm^-1. N.M.R. (CDCl₃): δ=1.5-2.7 (6H,m); 2.7-3.4 (1H,m).

References:

Lipha Lyonnaise Industrielle Pharmaceutique US5387709, 1995, A

FullText