1018452-78-2

Basic information

• Product Name: C₂₁H₂₃N₃OS
• Synonyms: C₂₁H₂₃N₃OS
• CAS NO: 1018452-78-2
• Molecular Weight: 365.499
• Mol File: 1018452-78-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₂₁H₂₃N₃OS(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₁H₂₃N₃OS(1018452-78-2)
• EPA Substance Registry System: C₂₁H₂₃N₃OS(1018452-78-2)

Safety Data

• Hazardous Substances Data: 1018452-78-2(Hazardous Substances Data)

Upstream product

• 69395-84-2 N-(diphenylmethyl)-cyanoacetamide 
• 590-42-1 tert-butyl isothiocyanate 

Relevant articles and documents

Enols and thioenols of substituted cyanomonothiocarbonylmalonamides: Structures, enolization vs. thioenolization, equilibria and conformations

Condensation of organic isothiocyanates with cyanoacetamides gave 24 N- and N′-substituted cyanomonothiocarbonylmalonamides in different tautomeric ratios i.e., amide-thioamides (TMA) R3NHCSCH(CN)CONR 1R2 (12), thioamide-enols of amides (E) R 3NHCSC(CN)=C(OH)NR1R2 (11) or amide-thioenols (TE) R3NHC(SH)=C(CN)CONR1R2 (13). The equilibrium constants (Kthioenol = [TE]/[TMA] and Kenol = [E]/[TMA]) in solution depend on R1, R2, R3 and the solvent. The %(E + TE) for NR1R2 increases in the order NMe2 2. The (Kthioenol + Kenol) in various solvents follows the order CCl4 > CDCl3 > C6D6 > THF-d8 > (CD3)2CO > CD3CN > DMF-d7 > DMSO-d6. The δ(OH) values are 16.46-17.43 and the δ(SH) values are 3.87-5.26 ppm in non polar solvents, e.g., CDCl3 and 6.34-6.97 ppm in THF-d8 and CD3CN. An intramolecular O-H...O hydrogen bond leads to the preferred Z-configuration of the enols, and an N-H...O bond stabilizes the thioenols' preferred E-configuration with a non-bonded SH in solution. X-Ray crystallography revealed that systems with high %(E + TE) in solution mostly display the enols 11 in the solid state and systems with lower %(E + TE) in solution display structure 12. The differences in δ(OH), δ(NH), Kenol and crystallographic data for analogous enol and thioenol systems are compared.