Category: 19853-10-2

Electric Literature of 19853-10-2, A common heterocyclic compound, 19853-10-2, name is 2-([1,1′-Biphenyl]-2-yl)acetonitrile, molecular formula is C14H11N, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 42 Preparation of 5-cyano-5-(1,1′-biphenyl-2-yl)pentyl chloride To a stirred solution of 4.3 g. of sodium amide in 300 ml. of toluene was added dropwise over thirty minutes a solution of 19.3 g. of (1,1′-biphenyl-2-yl)acetonitrile in 200 ml. of toluene. The reaction mixture was heated at reflux for three hours, and then cooled to room temperature and stirred while a solution of 18.1 g. of 4-bromobutyl chloride in 50 ml. of toluene was added dropwise over thirty minutes. Following complete addition, the reaction mixture was heated again to reflux and stirred for sixteen hours. The reaction mixture next was cooledto room temperature and added to 500 ml. of ice water. The product was extracted from the aqueous mixture into diethyl ether. The ethereal extracts were combined and the solvent was removed by evaporation to provide the product as an oil. The oil was distilled to give 16.5 g. of 5-cyano-5-(1,1′-biphenyl-2-yl)pentyl chloride. B.P. 141-165 C. at 0.06 torr.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Eli Lilly and Company; US4277471; (1981); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 19853-10-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 19853-10-2 name is 2-([1,1′-Biphenyl]-2-yl)acetonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A 1M solution of hydroxylamine hydrochloride in MeOH (15 ml) and 1M KOH solution in MeOH (15 ml) was combined at 0 C. After 10 minutes, the salt was removed by filtration and the filtrate was directly added to a flask containing 2-(biphenyl-2-yl)acetonitrile (0.50 g, 2.58 mmol) and was heated at 60 C. overnight. The cooled mixture was evaporated to dryness under reduced pressure and the residue was dissolve in EtOAc, washed with water, and brine, dried (MgSO4) and evaporated to dryness. The residue was dissolved in chloroform (10 ml) and treated with dimethyl but-2-ynedioate (0.403 g, 2.84 mmol). The mixture was stirred at 60 C. for 1 h and then evaporated to dryness. The residue was diluted with xylenes (10 ml) and heated at 130 C. for 90 min. The cooled filtrate was filtered, triturated with EtOAc and dried under vacuum to give the title product as an off-white solid (0.161 g; 18%). LCMS: m/z=337 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-([1,1′-Biphenyl]-2-yl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; F. HOFFMANN-LA ROCHE AG; BUSCHMANN, Helmut; WOLKERSTORFER, Andrea; SZOLAR, Oliver; HANDLER, Norbert; CUSACK, Stephen; SMITH, Mark; SO, Sung-Sau; US2014/38990; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts