Synthetic Route of 95-11-4, 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. 95-11-4 name is 5-Norbornene-2-carbonitrile, 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.
Ortho-dichlorobenzene (958 g) was added into a five-neck flask which is equipped with a reflux cooling tube,stirring blades, a thermometer, a gas-blowing tube and a raw material-injecting tube, and had an inner volume of 2 liter,154.2 g (1.0 mol) of 2,5-bisaminomethyl-bicyclo[2.2.1]heptane and 2,6-bisaminomethyl-bicyclo[2.2.1]heptane which hadbeen obtained in Example 2 and ortho-dichlorobenzene (702 g) were prepared in a raw material tank. Next, a reactioncontainer was heated to 120C at 0.1 MPa, adding of hydrochloric acid gas from a hydrochloric acid-blowing tube at arate of 43.8 g/hr and adding of an amine diluted by a solvent from the raw material tank using a raw material-injectingpump at a rate of 428.1 g/hr were initiated at the same time, and the total amount was added over 2 hours. Furthermore,aging was carried out for 1 hour while adding hydrochloric acid gas at 20 g/hr. After the completion of the reaction,subsequently, hydrochloride reaction mass was heated to 160C, phosgene was blown in from a phosgene-blowingtube at 100 g/hr (1.0 mol/hr), and a reaction was caused for 6 hours while maintaining the temperature. After thecompletion of the reaction, unreacted phosgene and hydrochloric acid gas in the system were purged using nitrogen,and the solvent was removed, thereby obtaining a solution (200.9 g) including 2,5-bisisocyanate methyl-bicyclo[2.2.1]heptane and 2,6-bisisocyanate methyl-bicyclo[2.2.1]heptane. Furthermore, distillation was carried out under reducedpressure, and a mixture (175.7 g) of 2,5-bisisocyanate methyl-bicyclo[2.2.1]heptane and 2,6-bisisocyanate methylbicyclo[2.2.1]heptane having a purity of 99.0% was obtained. An 1H-NMR chart is illustrated in Fig. 3.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Norbornene-2-carbonitrile, and friends who are interested can also refer to it.
Reference:
Patent; Mitsui Chemicals, Inc.; KUMA, Shigetoshi; SAKATA, Michiharu; TOKUNAGA, Kouichi; SHIMAKAWA, Chitoshi; KAKINUMA, Naoyuki; FURUYA, Masayuki; TANAKA, Mamoru; EP2708527; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts