Synthesis of glutaronitrile

Preparation of glutaronitrile

Preparation of glutaronitrile

Preparation of glutaronitrile

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.  0.25 mole of 1,3-dichloropropane is slowly added to the stirred mixture causing the temperature to increase immediately. The rate of addition is such that the temperature of the reaction did not go above about 160º C. After all the 1,3-dichloropropane is added the mixture is stirred for additional 10 min. more, or until the temperature dropped below 50º C. After the reaction is complete the mixture is cooled to room temperature and 150 ml. of chloroform is added to the flask and this mixture is then poured into saturated sodium chloride solution. Enough water was added to dissolve precipitated salt and the chloroform layer was separated. The aqueous layer was extracted once with chloroform. The combined extracts were then washed twice with sodium chloride solution, dried, and distilled at 101-102º C/1.5 mmHg yielding 67% of the final product.

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

IUPAC Name

pentanedinitrile

InChI

InChI=1S/C5H6N2/c6-4-2-1-3-5-7/h1-3H2

InChI Key

ZTOMUSMDRMJOTH-UHFFFAOYSA-N

Canonical SMILES

C(CC#N)CC#N

Depositor-Supplied Synonyms

Glutaronitrile, PENTANEDINITRILE, 544-13-8, 1,3-Dicyanopropane, Glutarodinitrile, Glutaric acid dinitrile, 1,3-Trimethylenedinitrile, Pyrotartaric acid nitrile, Trimethylene dicyanide, ZTOMUSMDRMJOTH-UHFFFAOYSA-N, NSC 3807, EINECS 208-861-6, SBB068303, BRN 1738385, AI3-07024, 903903-26-4, Dicyanopropane, Glutaronitrle, Glutaric dinitrile, PubChem15199, ACMC-1APXF, AC1L1WEB, WLN: NC3CN, propane-1,3-dicarbonitrile, UNII-01ZI68F3CQ, 01ZI68F3CQ, 130621_ALDRICH, 49730_FLUKA, CTK1H0306, NSC3807, MolPort-001-779-793, NSC-3807, ZINC1672862, ANW-32069, ZINC01672862, AKOS000156040, AJ-29271, AK114550, AN-25536, I475, KB-77552, OR035424, OR383050, DB-071848, LS-157460, ST2419400, TR-019241, FT-0626736, FT-0657164, G0072, 4-02-00-01941 (Beilstein Handbook Reference), A830168, A843532, I14-5923, S14-1136, InChI=1/C5H6N2/c6-4-2-1-3-5-7/h1-3H

Removed Synonyms

C5H6N2, CID10994

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