322406-99-5

Basic information

• Product Name: 2-carbamoylmethylthio-3-cyano-4-(4-cyanophenyl)-5-ethoxycarbonyl-6-methyl-1,4-dihydropyridine
• CAS NO: 322406-99-5
• Molecular Weight: 382.443
• Mol File: 322406-99-5.mol

Chemical Properties

• CAS DataBase Reference: 2-carbamoylmethylthio-3-cyano-4-(4-cyanophenyl)-5-ethoxycarbonyl-6-methyl-1,4-dihydropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-carbamoylmethylthio-3-cyano-4-(4-cyanophenyl)-5-ethoxycarbonyl-6-methyl-1,4-dihydropyridine(322406-99-5)
• EPA Substance Registry System: 2-carbamoylmethylthio-3-cyano-4-(4-cyanophenyl)-5-ethoxycarbonyl-6-methyl-1,4-dihydropyridine(322406-99-5)

Safety Data

• Hazardous Substances Data: 322406-99-5(Hazardous Substances Data)

Upstream product

• 144-48-9 iodacetamide 
• 322406-96-2 3-cyano-4-(4-cyanophenyl)-5-ethoxycarbonyl-6-methyl1,4-dihydropyridine-2(3H)-thione 
• 141-97-9 ethyl acetoacetate 
• 89809-67-6 ethyl (E/Z)-2-(4-cyanobenzylidene)-3-oxobutanoate 
• 105-07-7 4-cyanobenzaldehyde 

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 properties of 3-cyano-4-(4-cyanophenyl)-1,4-dihydropyridine-2(3H)-thiones

Piperidinium 3-cyano-4-(4-cyanophenyl)-1,4-dihydropyridine-2(3H)-thiolates were obtained by the condensation of 1,3-dicarbonyl compounds, 4-cyanobenzaldehyde, and cyanothiacetamide in the presence of an equimolar amount of piperidine. The acidification of these thiolates gave the corresponding1,4-dihydropyridine-2(3H)-thiones and pyridine-2(1H9-thione. Alkylation of 1,4-dihydropyridine-2-thiolates or the reaction mixture of the three-carbon condensation using iodacetamide gave 2-carbamoylmethylthio-1,4,5,6-tetrahydro- or 1,4-dihydropyridines, which were characterized by their conversion to 4,7-dihydrothieno[2,3-b]pyridines.