Synthesis of succinonitrile (butanedinitrile, 1,2-dicyanoethane)

Preparation of succinonitrile

Preparation of succinonitrile ( butanedinitrile, 1,2-dicyanoethane)

Preparation of succinonitrile ( butanedinitrile, 1,2-dicyanoethane)

66 grams of potassium cyanide was dissolved in 100 ml of water and added to 200 ml of ethyl alcohol. A solution of 200 g of ethylene bromide, and 200 ml of ethyl alcohol was placed in a 500 ml reaction flask and connected with a reflux condenser. Then the alcoholic solution of potassium cyanide was added slowly to the solution of ethylene bromide in ethanol from the dropping funnel. Little heat was evolved indicating little or no immediate reaction. After adding additional 100 ml of ethyl alcohol to insure complete solution of the ethylene bromide the mixture was heated on the water bath for two-three hours and fairly large precipitation of potassium bromide appeared. The solution was filtered, the ethyl alcohol evaporated and the crude succinonitrile was extracted with ether. After drying with calcium chloride and removing ether by evaporation, extracted succinonitrile was distilled. The fraction boiling at 260-270° C was collected.

The synthesis of amino acids, by B. B. Wilcox, 29-30, 1904

By slightly improved method succinonitrile is prepared by using DMSO:

Preparation of succinonitrile

Preparation of succinonitrile

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 1,2-dichloroethane 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 1,2-dichloroethane 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 114º C/3.4mmHg yielding 56% of the final product.

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

IUPAC Name

butanedinitrile

InChI

InChI=1S/C4H4N2/c5-3-1-2-4-6/h1-2H2

InChI Key

IAHFWCOBPZCAEA-UHFFFAOYSA-N

Canonical SMILES

C(CC#N)C#N

MeSH Synonyms

succinonitrile

Depositor-Supplied Synonyms

SUCCINONITRILE, Butanedinitrile, 110-61-2, Ethylene cyanide, Deprelin, 1,2-Dicyanoethane, Ethylene dicyanide, Succinil, Dician, Dinile, Disuxyl, Evanex, Succinodinitrile, Suxil, s-Dicyanoethane, Succinic dinitrile, Succinic acid nitrile, 1,4-Butanedinitrile, Succinic acid dinitrile, Sukcinonitril, USAF A-9442, Ethane, 1,2-dicyano-, Sukcinonitril [Czech], NSC 4852, UNII-1R479O92DO, CCRIS 4720, HSDB 7190, IAHFWCOBPZCAEA-UHFFFAOYSA-N, EINECS 203-783-9, BRN 1098380, AI3-06591, Dicyanoethane, sym-Dicyanoethane, Ethane,2-dicyano-, PubChem19068, ACMC-1BSCP, NCCH2CH2CN, DSSTox_CID_6059, WLN: NC2CN, ethane-1,2-dicarbonitrile, AC1L1Q6F, AC1Q4S5W, DSSTox_RID_77999, DSSTox_GSID_26059, KSC175O5L, MLS002152938, 160962_ALDRICH, Jsp000810, CHEMBL1562258, CTK0H5755, NSC4852, MolPort-001-787-937, 1R479O92DO, BB_SC-5735, NSC-4852, Tox21_200635, ANW-16173, AR-1L5711, BBL011331, LS-510, SBB067430, STL146417, ZINC01680419, AKOS005721200, MCULE-5570794181, NE10134, RTR-034032, NCGC00091567-01, NCGC00091567-02, NCGC00258189-01, AK163360, AN-22612, CAS-110-61-2, CJ-06266, KB-80755, SMR001224533, DB-060019, TR-034032, FT-0654273, S0109, ST24049314, EN300-35675, I14-3315, InChI=1/C4H4N2/c5-3-1-2-4-6/h1-2H, 191362-21-7

Removed Synonyms

CID8062, R256, 4-02-00-01923 (Beilstein Handbook Reference), 1118-77-0

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