Synthesis of 2-cyanobutane

Preparation of 2-cyanobutane

Preparation of 2-cyanobutane

Preparation of 2-cyanobutane

30 g of dry sodium cyanide (dried at 110º C overnight a) are mixed with 150 ml of dry dimethyl sulfoxide. The mixture is added to the flask fitted with a stirrer, reflux condenser, dropping funnel, and thermometer. The thick reaction slurry is heated to 90º C and the heating then  is stopped.  0.5 mole of 2-chlorobutane  is slowly added to the stirred mixture during 30 min. The temperature of the refluxing reaction mixture slowly increased as nitrile was formed. Refluxing continued as the temperature slowly rose to 150 ºC after 3 hr. reaction time. After the reaction is complete the mixture is poured into water and the product extracted several times with chloroform or ethyl ether. The extract is washed several times with saturated sodium chloride solution, dried over calcium chloride, and the 2-cyanobutane is distilled at 125-126 ºC yielding 69% of the final product.

J. Org. Chem., 1960, 25 (2), pp 257–258

IUPAC Name

2-methylbutanenitrile

InChI

InChI=1S/C5H9N/c1-3-5(2)4-6/h5H,3H2,1-2H3

InChI Key

RCEJCSULJQNRQQ-UHFFFAOYSA-N

Canonical SMILES

CCC(C)C#N

MeSH Synonyms

2-methylbutanone cyanohydrin

Depositor-Supplied Synonyms

2-Methylbutanenitrile, 2-Methylbutyronitrile, 2-Cyanobutane, 18936-17-9, 2-Methylbutanone cyanohydrin, alpha-Methylbutyronitrile, sec-Butyl Cyanide, Butanenitrile, 2-methyl-, s-butyl cyanide, Butyronitrile, 2-methyl-, RCEJCSULJQNRQQ-UHFFFAOYSA-N, EINECS 242-687-1, NSC 165615, 2-methylbutylnitrile, ACMC-20apgp, Butanenitrile,2-methyl-, ACMC-1CFV5, .alpha.-Methylbutyronitrile, AC1L1H8S, AC1Q2S07, CHEBI:61669, CTK4E0118, MolPort-001-783-994, Butanenitrile, 2-methyl- (9CI), 9871AA, ANW-23442, NSC165615, AKOS009157026, NE10127, NSC-165615, AK109193, KB130025, LS-48262, OR020324, OR129525, KB-231693, TC-112187, M0706, ST24028101, EN300-69936, 3B3-047071, I14-102887

Removed Synonyms

(S)-2-methylbutyronitrile, C5H9N, (S)-(+)-2-Methylbutyronitrile, CID29339, C547130, 25570-03-0

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