Synthesis of pimelonitrile

Preparation of pimelonitrile

Preparation of pimelonitrile

Preparation of pimelonitrile

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 1,5-dichloropentane 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 1,5-dichloropentane 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 149º C/1.0 mmHg yielding 75% of the final product.

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

IUPAC Name

heptanedinitrile

InChI

InChI=1S/C7H10N2/c8-6-4-2-1-3-5-7-9/h1-5H2

InChI Key

LLEVMYXEJUDBTA-UHFFFAOYSA-N

Canonical SMILES

C(CCC#N)CCC#N

Depositor-Supplied Synonyms

Heptanedinitrile, 1,5-Dicyanopentane, 646-20-8, PIMELONITRILE, Pentamethylene dicyanide, Pimelic acid dinitrile, LLEVMYXEJUDBTA-UHFFFAOYSA-N, NSC 5392, EINECS 211-469-8, SBB068424, BRN 1742138, AI3-28713, pentane-1,5-dicarbonitrile, 1,7-heptanedinitrile, AC1L1ZX6, AC1Q4S7X, ACMC-1B23G, D79004_ALDRICH, KSC356M4J, SCHEMBL818520, UNII-3D5H23A27Q, 80530_FLUKA, CTK2F6644, NSC5392, MolPort-001-783-826, 3D5H23A27Q, NSC-5392, ZINC1680886, ANW-34920, MFCD00001980, ZINC01680886, AKOS009157293, CS19974, MCULE-5676023796, MP-0021, RTR-022114, TRA0053928, AJ-29659, AK-76744, AN-20471, CJ-06292, KB-64585, LP057627, LS-74315, OR037002, DB-027338, ST2413112, TL8004603, TR-022114, FT-0653989, P0049, ST51038577, Z4991, EN300-55306, A834830, I14-6673, 3B1-007003, InChI=1/C7H10N2/c8-6-4-2-1-3-5-7-9/h1-5H

Removed Synonyms

C7H10N2, CID12590, 4-02-00-02006 (Beilstein Handbook Reference)

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