Cyanoethylation ester

Cyanoethylthiouronium hydrochloride Carbamimidothioic acid, 2-cyanoethyl ester, monohydrochloride salt (8,9) (6634-40-8)... 

Add 8.0g (10.0ml, 0.15 mol) of redistilled acrylonitrile (Expt 5.161, Note (1)) to a stirred solution of diethyl propylmalonate (30.2 g, 0.15 mol) (Expt 5.132) and of 30 per cent methanolic potassium hydroxide (4.0 g) in t-butyl alcohol (100 g). Keep the reaction mixture at 30-35 °C during the addition and stir for a further 3 hours. Neutralise the solution with 2 M-hydrochloric acid, dilute with water and extract with ether. Dry the ethereal extract with anhydrous sojdium sulphate and distil off the ether the residue [diethyl (2-cyanoethyl)-propylmalonate 11 g] solidifies on cooling in ice, and melts at 31—32 °C after recrystallisation from ice-cold ethanol. Boil the cyanoethyl ester (10 g) under reflux with 40 ml of 48 per cent hydrobromic acid solution for 8 hours, and evaporate the solution almost to dryness under reduced pressure. Add sufficient water to dissolve the ammonium bromide, extract several times with ether, dry the ethereal extract and distil off the solvent. The residual oil (4.5 g, 66%) soon solidifies upon recrystallisation from water, pure 2-propylglutaric acid, m.p. 70 °C, is obtained. 

The cyanoethylation of polysaccharides has been studied extensively in starch and cellulose. The hydroxyl groups (typically the C-4) on the molecule react with acrylonitrile in the presence of alkali to form a cyanoethyl ester. O-Cyanoethylated cellulose is used in the paper industry to enhance the mechanical strength, heat resistance, and microbiological resistance of the paper. Cyanoethylated starch is used in the textile industry. 

In another experiment (14), 6.4 g. of cyanoethyl ester was reduced to i3-alanine by hydrogenation at room temperature and atmospheric pressure with a catalyst containing 30 mg. of palladium and 500 mg. of polyvinyl alcohol. 

On the other hand, the use of 1-cyanoethyl ester derivative 43 for the glycosylation of 48 resulted in /3-exclusive formation of Neu5Ac-(2-6)-Glc sequence 49 in high yield, while in MeCN the production of a-glycoside was preferred [37]. 

As base. Because of its high basicity in aprotic media, TBAF is capable of cleaving 2-cyanoethyl esters in THF-DMF and acts as a catalyst in epoxide opening. ... 

Vitamin Bg and Related Compounds.—Analogues of pyridoxol and pyridoxal phosphates in which the 5 -methylene (35) or the 5 -phosphate group (36) have been modified have been used to study the substrate specificity of pyridoxine phosphate oxidase. The methylene analogues acted as substrates whereas (36) or the 2-cyanoethyl ester of pyridoxol... 

N-Cyanoethyl-N-acetoxyethyl aniline. See Cyanoethylacetoxyethylaniline Cyanoethyl acrylate. See 2-Cyanoethyl acrylate 2-Cyanoethyl acrylate CAS 106-71-8 EINECS/ELINCS 203-426-7 Synonyms Acrylic acid, 2-cyanoethyl ester Acrylic acid, ester with hydracrylonitrile Cyanoethyl acrylate 2-Cyanoethyl propenoate Hydracrylonitrile, acrylate 2-Propenoic acid, 2-cyanoethyl ester Classification Acrylic Empirical C6H7NO2 Formula CHziCHCOOCHzCHzCN Properties Liq. sol. in water m.w. 125.14 dens. 2.0690 f.p. -16.9 C flash pt. 255 F (124 C) Toxicology LD50 (oral, rat) 180 mg/kg, (skin, rabbit) 220 pl/kg toxic by ing. and inh. primary irritant mod. to severe skin irritant mild eye irritant corrosive causes burns possible sensitizer TSCA listed Precaution Combustible Hazardous Decomp. Prods. Heated to decomp, emits NOx, CN-... 

Protection of carboxyl groups as 2-cyanoethyl esters OCH2CH2CN - OH... 

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