793683-47-3

Basic information

• Product Name: 2-carbamoylmethylthio-5-ethoxycarbonyl-6-hydroxy-6-methyl-4-(4-nitrophenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acid nitrile
• CAS NO: 793683-47-3
• Molecular Weight: 420.446
• Mol File: 793683-47-3.mol

Chemical Properties

• CAS DataBase Reference: 2-carbamoylmethylthio-5-ethoxycarbonyl-6-hydroxy-6-methyl-4-(4-nitrophenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acid nitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-carbamoylmethylthio-5-ethoxycarbonyl-6-hydroxy-6-methyl-4-(4-nitrophenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acid nitrile(793683-47-3)
• EPA Substance Registry System: 2-carbamoylmethylthio-5-ethoxycarbonyl-6-hydroxy-6-methyl-4-(4-nitrophenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acid nitrile(793683-47-3)

Safety Data

• Hazardous Substances Data: 793683-47-3(Hazardous Substances Data)

Upstream product

• 144-48-9 iodacetamide 
• 15802-69-4 2-(4-nitrophenylmethylene)acetoacetic acid ethyl ester 
• 15802-69-4 ethyl 2-(4-nitrobenzylidene)-3-oxobutanoate 

Relevant articles and documents

Synthesis, structure, and electrochemical characteristics of 4-aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid nitriles

We have obtained 4-aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-1,4- dihydropyridine-3-carboxylic acid nitriles by S-alkylation of the corresponding 2-thioxo-1,2,3,4-tetrahydropyridine-3-carboxylic acid nitrile by iodoacetamide or one-pot multicomponent synthesis methods: condensation of 2-arylidene-acetoacetic acid ethyl ester, 2-cyanothioacetamide, piperidine, and iodoacetamide; acetoacetic acid ethyl ester, 3-aryl-2-cyanothioacrylamide, piperidine, and iodoacetamide; acetoacetic acid ethyl ester, an aromatic aldehyde, 2-cyanothioacetamide, piperidine, and iodoacetamide. We have carried out a comparative analysis of the capability of 2-alkylthio-4-aryl-5- ethoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid nitriles for electrochemical oxidation as a function of the electronic properties of the aryl substituent in the 4 position of the heterocycle and the 2-alkylthio substituent. X-ray diffraction data indicate the existence of a hydrogen bond between the C=O of the 2-carbamoylmethylthio substituent and the NH of the hydrogenated heterocycle, which explains the more facile oxidation of the studied compounds compared with 2-methylthio-substituted 1,4-dihydropyridines.

Synthesis and electrochemical oxidation of nitriles of 4-aryl-2- carbamoylmethylthio-5-ethoxy-carbonyl-1,4-dihydropyridine-3-carboxylic acids

Nitriles of 4-aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-6-hydroxy-1,4,5, 6-tetrahydropyridine-3-carboxylic acids were obtained by the alkylation of 1,4,5,6-tetrahydropyridine-2-thiolate with iodoacetamide or by a three-component synthesis by condensing 2-arylmethylene-1,3-dicarbonyl compounds with 2-cyanothioacetamide in the presence of piperidine with subsequent reaction with iodoacetamide. Nitriles of 4-aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-1,4- dihydropyridine-3-carboxylic acids were obtained by the dehydration of 6-hydroxy-1,4,5,6-tetrahydropyridines or with a one-reactor three-component system from 2-cyano-3-(4-methoxyphenyl)thioacrylamide, 1,3-dicarbonyl compounds, and iodoacetamide. The electrochemical oxidation of the synthesized nitriles was investigated and it was established that derivatives of 1,4,5,6- tetrahydropyridine as a rule are oxidized readily to the corresponding 1,4-dihydropyridines. A comparative analysis has been carried out of the ability of hydrogenated pyridines to be oxidized electrochemically depending on the electron-withdrawing properties of the substituents in the heterocycle.