ジフェニルアセトニトリル

化学的特性Diphenylacetonitrile is a white to creamy or faint yellow crystalline powder, Soluble in ethanol, ether. It is obtained by bromination and condensation of phenylacetonitrile. Diphenylacetonitrile is mainly used as an intermediate to manufacture API which deals in treatment of respiratory stimulant. It is used to manufacture APIs like stomach amine, Aminepentamide Sulphate, Diphenoxylate, Diphenylacetaldehyde, Doxapram, Loperamide, Methadone.

用途有機合成原料。

使用Mathadone (M225865) impurity. Used in synthesis of methadone, antispasmodics and other pharmaceuticals.Diphenylacetonitrile is used to synthesize isocyanate, which is further prepared into UV paint, PU paint, transparent elastomer and adhesive, etc. In addition, it is also used in polyamide and epoxy resin industries.

一般的な説明Diphenylacetonitrile can be prepared in good yield by the dehydration of the amide of diphenyl acetic acid with phosphorous oxychloride.

製造方法In a 100 mL, nitrogen-flushed pear flask was added indium(III) bromide (2.0 mmol, 10 mol %) in CH2Cl2 (40 mL) to give a white suspension. To this at room temperature was added trimethylsilyl cyanide (40 mmol, 2.0 equiv.), followed by dropwise addition of alcohol (20 mmol, 1.0 equiv.) to give a moderate exothermic reaction. The mixture slowly turned clear, and TLC showed mostly the desire product. Saturated NaHCO3 was added and the mixture was concentrated in vacuo to remove the volatiles. The residue was partitioned between saturated NaHCO3 and ethyl acetate, and the aqueous layer was extracted one more time with ethyl acetate. Combined organic layers were dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography on silica gel (5% ethyl acetate/hexanes) to give the desired Diphenylacetonitrile.

製造方法Diphenylacetonitrile can be prepared in good yield by the dehydration of the amide of diphenyl acetic acid with phosphorous oxychloride. Diphenylacetonitrile undergoes anhydrous condensation with ethyl-4-bromo-butyrate. This is followed by its hydrolysis in alkaline medium that is used in the quantitative determination of 3-cyano-3,3-diphenylpropionic acid.

純化方法Crystallise the nitrile from EtOH or pet ether (b 90-100o). [Beilstein 9 H 674, 9 IV 2505.]