Cyano-acetic acid

A solution of 69g of sodium in 1,380 ccof absolute alcohol is mixed with 257.4 g of /3-methyl-thioethyl-d -methyl)-n-butvl-cyano-acetic acid ethyl ester and 114 g of thiourea and the whole mass boiled under reflux with stirring for six hours. After concentration under vacuum the residue is taken up in 1.5 liters of water and shaken up thrice, each time with 300 cc of ether. The aqueous alcoholic layer is stripped, under vacuum, of the dissolved ether and mixed with 300 cc of 30% acetic acid under stirring and ice cooling. The precipitated material is sucked off, washed with water, dried and recrystallized from isopropyl alcohol. The thus obtained j3-methvl-thioethyl-(1 -methyD-n-butyl-cyano-ecetyl thiourea forms yellowish green crystals having a melting point of 229°C to 230°C. 

By coelectrolysis of polymethacrylic acid with e-acetaminocaproic acid or cyano-acetic acid the alkylacetamido- or cyanomethyl group can be grafted on to the main chain of the polymer [205]. 

Ammonium acetate as catalyst for condensation of furfural with cyano-acetic acid, 40, 47... 

S3mthesis of Xanthine.— The synthesis of xanthine which is the immediate mother substance of theobromine, theophylline and caffeine has been accomplished as follows Starting with urea or carbamide, this is treated with cyano acetic acid in the presence of phosphorus oxychloride whereby the cyan acetyl radical is introduced into urea. The cyan acetyl urea by treatment with sodium hydroxide yields an isomeric imino compound. 

Sodium cyanide also is used in chemical synthesis. As previously mentioned, sodium cyanide is used to produce the sequestrant EDTA [82]. Chloroacetic acid reacts with sodium cyanide in the presence of soda ash to yield cyano-acetic acid. Sodium cyanide reacting with a-chloromethylnaphthalene followed by hydrolysis yields a-naphthaleneacetamide and the corresponding carboxylic acid these are two of several common plant hormones, growth acceler-... 

HNOa-Cyano-acetic acid, 66, 2,4-Di mteo phenyl-hydra zone,... 

Ethyl (1-methyl-A]-buteny )cyano-acetic acid ethyl ester Vinbarbital sodium 1-Ethyl-6,7-methylenedioxy-4-(1H)-oxocinnoline-3-carbonitrile Cinoxacin... 

When malononitrile was used as a substrate, a high conversion of 98% was obtained after 12 h, whereas almost no activity was observed in the conversion of ethyl cyanoacetate and cyano-acetic acid tert-butyl ester, suggesting that the catalyst was size selective. The observation of reactant shape selectivity revealed that the catalytic turnovers take place in the MOF channels rather than at the outer surface of the MOF particles. Upon desolvation, for example, by the removal of water... 

N-(3-Phenylallylidene)aniline allowed to react 24 hrs. at room temp, with cyano-acetic acid in dry benzene -> product. Y 80%. F. e. s. N. Singh and J. S. Sandhu, J. Indian Chem. Soc. 46, 751 (1969). 

Other notable reports of annulations involving nitriles were concerned with the preparation of y-lactones prepared from cyano-acetic acid derivatives and olefins in the presence of manganese(III) acetate.The "carbon-zip" ring expansion of... 

N-[3 -(4-Methy Iphenyl)-1 -phenyl-1 H-pyrazol-4-methylidene] -cyanoacetic acid hydrazide 154 was synthesised in an excellent yield by condensing 3-(4-methylphenyl)- -phenyl-lH-pyrazole-4-carboxaldehyde with cyano-acetic acid hydrazide. This intermediate was converted to the 4-amino-3-aryl-5-[3-(4-methylphenyl)-1 -phenyl-1 H-pyrazol-4-methylidenehydrazinocarbonyl] -thiazole-2(3H)-thiones 155 (Scheme 72), following the method described by Gewald, it involved the reaction of the cyanoacetic acid hydrazide derivative 154 with sulphur and the appropriate aryl isothiocyanate in the presence of triethylamine as a basic catalyst. Cyclisation of 145 to the 3-aryl-6-[3-(4-methylphenyl)-l-phenyl-1 H-pyrazol-4-methylideneamino] -2-thioxo-2,3 -dihydrothiazolo [4,5 -djpyrimidin-7(6H)-ones 156 was achieved by heating the former with a mixture of triethyl orthoformate and acetic anhydride (1 1) [4],... 

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