204690-21-1

Basic information

• Product Name: (Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethanamide
• Synonyms: (Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethanamide
• CAS NO: 204690-21-1
• Molecular Weight: 320.369
• Mol File: 204690-21-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethanamide(204690-21-1)
• EPA Substance Registry System: (Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethanamide(204690-21-1)

Safety Data

• Hazardous Substances Data: 204690-21-1(Hazardous Substances Data)

Upstream product

• 621-03-4 cyanoacetanilide 
• 23060-14-2 diethyl 2-mercaptosuccinate 

Downstream Products

• 285133-46-2 (E)-2-bromo-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethanamide 
• 235423-16-2 (2Z,5Z)-N-phenyl (5-ethoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)ethanamide 
• 235423-20-8 (2E,5Z)-N-phenyl (5-ethoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)ethanamide 
• 285133-47-3 (Z)-2-bromo-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethanamide 

Relevant articles and documents

Regioselective synthesis and spectral characterization of ethyl (Z)- and (E)-2-alkylidene-4-oxothiazolidine-5-acetate derivatives. Solvent effects on the Z-E isomerization

The title compounds containing an exocyclic double bond of exclusively the Z-configuration were prepared in anhydrous ethanol by the regio-selective base catalyzed reaction of diethyl 2-mercaptobutanedioate with nitrile precursors possessing an acidic α-hydrogen. The 1H NMR data indicating the presence of both geometrical isomers in primarily nonpolar media favoring the E-form are presented in terms of the solvent influence on intra- and intermolecular H-bonding and stereochemical outcome of the reaction.

Reactivity of substituted 4-oxothiazolidine derivatives in electron transfer reactions: A spectroelectrochemical study and mechanistic aspects

The electrochemical reduction of (5-ethoxycarbonylmethylidene-4- oxothiazolidin-2-ylidene)-N-phenylethanamide (designated as compound 2) as a mixture of the (2E,5Z) and (2Z,5Z) isomers in DMSO to (Z)-(5- ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethanamide (compound 1) was investigated by electrochemical (cyclic voltammetry with a stationary and rotating disc electrode) and spectroelectrochemical (electron paramagnetic resonance and UV-vis absorption) in situ techniques. A reduction mechanism, which consisted of an ECE-Disp sequence and was followed by the protonation of the strong electrogenerated base dianion, was proposed. The results indicate the presence of the same intermediate species, the dianion, when starting from either compound 2 by electrochemical reduction, or from compound 1 in presence of TBOH in DMSO. The suggested mechanism, which is based on the experimental results, corroborated with the gas phase and the solvent-dependent semiempirical PM3-MO calculations, was rationalized in terms of the electronic structure and the reactivity of the intermediate species involved.

Configurational isomerization of push-pull thiazolidinone derivatives controlled by intermolecular and intramolecular RAHB: 1H NMR dynamic investigation of concentration and temperature effects

1H NMR spectroscopy was used to investigate hydrogen bonding in the structurally related (Z)- and (E)-5-substituted-2-alkylidene-4-oxothiazolidines in polar and apolar solvents. The equilibrated mixtures of these typical push-pull alkenes consi