32607-35-5

Upstream product

• 52060-58-9 N-p-Tolyl-N'-(carboxymethyl)thiourea 
• 56-40-6 glycine 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 75390-40-8 tetra-p-tolyloxalic amidine 
• 24066-82-8 ethyl 2-isothiocyanatoacetate 
• 99006-58-3 {2-Thioxo-3-p-tolyl-4,5-bis-[(Z)-p-tolylimino]-imidazolidin-1-yl}-acetic acid ethyl ester 
• 99006-63-0 (4,5-Dioxo-2-thioxo-3-p-tolyl-imidazolidin-1-yl)-acetic acid ethyl ester 
• 111651-82-2 ethyl 2‐(3‐(p‐tolyl)thioureido)acetate 

Downstream Products

• 102311-45-5 5-[1]naphthylmethyl-3-p-tolyl-imidazolidine-2,4-dione 
• 102241-41-8 5-[1]naphthylmethylene-3-p-tolyl-imidazolidine-2,4-dione 
• 325153-43-3 5-[1-Dimethylamino-meth-(Z)-ylidene]-2-methylsulfanyl-3-p-tolyl-3,5-dihydro-imidazol-4-one 
• 325153-40-0 5-[(Z)-(dimethylamino)methylidene]-3-(4-methylphenyl)-2-thioxoimidazolidin-4-one 
• 351034-14-5 5-[1-Phenyl-meth-(Z)-ylidene]-2-thioxo-3-p-tolyl-imidazolidin-4-one 
• 351034-16-7 5-[1-Benzo[1,3]dioxol-5-yl-meth-(Z)-ylidene]-2-thioxo-3-p-tolyl-imidazolidin-4-one 
• 351034-20-3 5-[1-Thiophen-2-yl-meth-(Z)-ylidene]-2-thioxo-3-p-tolyl-imidazolidin-4-one 
• 53865-31-9 5-(2-nitro-benzylidene)-2-thioxo-3-p-tolyl-imidazolidin-4-one 
• 53865-41-1 3-p-Tolyl-5-(4'-nitrobenzyliden)-2-thio-hydantoin 
• 61442-33-9 5-naphthalen-1-ylmethylene-2-thioxo-3-p-tolyl-imidazolidin-4-one 
• 858202-83-2 1-acetyl-2-thioxo-3-p-tolyl-imidazolidin-4-one 

Relevant academic research and scientific papers

Glycosylation of 2-thiohydantoin derivatives. Synthesis of some novel S-alkylated and S-glucosylated hydantoins

3-Aryl-5-((Z)-arylidene)-3-aryl-2-(2-methylthioethyl)-2-thiohydantoins 3a-f and 3-aryl-5-((Z)-arylidene)-2-(2′,3′,4′,6′-tetra-O- acetyl-β-D-glucopyranosyl)-2-thiohydantoins 7a-n were prepared from the reaction of 3-aryl-5-((Z)-arylidene)-2-thiohydantoins

Molecular rearrangement of sulfur compounds pyrolysis of 2-(n-substituted carboxamidomethylthio) 5-phenyl-1,3,4-oxadiazole derivatives

Pyrolysis of 2-(N-phenyl carboxamidomethylthio) 5-phenyl-1,3,4-oxadiazole at ca 200°C in a sealed tube affords carbon dioxide, hydrogen sulfide, water, benzonitrile, benzamide, aniline, p-aminoacetophenone, indole, thioglycolic acid, 3-phenyl-2-thiohydantoin and 2-mercaptoquinazolinone. Furthermore pyrolysis of 2-(N-p-tolyl carboxamidomethylthio)5-phenyl-1,3,4-oxadiazole give rise to analogous products. A free radical mechanism has been suggested to account for the obtained products.

A New Method of Synthesis of 3-Monosubstituted-2-thiohydantoins and -Hydantoins

A new method of synthesis of 3-monosubstituted derivatives of 2-thiohydantoin and hydantoin in reaction of isothiocyanate or isocyanate glycin ethyl ester with primary aliphatic and aromatic amines has been described. Crude products were obtained with high yield and purity. The structure of these compounds was confirmed by spectral methods. Key words: 2-thiohydantoin, hydantoin, isothiocyanate glycin ethyl ester, isocyanate glycin ethyl ester

On the Reaction of Oxalic Amidines with Carbonic Acid Derived Heterocumulenes to Imidazolidine-Derivatives

A useful synthetic route to nonsymmetric derivatives of imidazolidine (derivatives of parabanic acid) is demonstrated by the reaction of tetraarylated oxalic amidines 1 with different alkyl- and aryl substituted isothiocyanates 4, isoselenocyanates 31, and carbodiimides 30.Acylisothiocyanates 9 react differently leading to a mixture of three cycloacylation products 12, 13 and 14.Silylated heterocumulenes such as 25 and 26 react with 1 to give 28 and 29 transsilylation.Based on the 13C-n.m.r. spectroscopic investigation of the reaction between 1a and methyl isothiocyanate and phenyl isothiocyanate respectively a mechanism is proposed.

MECHANISM OF BASE-CATALYZED CYCLIZATION OF ETHYL N-(SUBSTITUTED AMINOCARBONYL)GLYCINATES

The cyclization rate constants have been measured of substituted ethyl N-(phenylaminocarbonyl)-, N-(alkylaminocarbonyl)-, and N-(phenylaminothiocarbonyl)glycinates RNHCXNHCH2CO2C2H5 (X=O,S).Logarithms of these constants increase with decreasing basicity of the amines down to the value of pKa(RNH2) = 5.5.The rate-limiting step of the reaction is formation of the tetrahedral intermediate.With ethyl N-(phenylaminocarbonyl)glycinates (whose pKa(RNH2) values are higher) this dependence, on the contrary, slightly decreases, and the acid-catalyzed splitting off of ethoxy group from the cyclic intermediate becomes rate-li miting.The cyclization rate of a series of ethyl N-(phenylaminothiocarbonyl)glycinates is practically independent of the pKa(RNH2) values, the change in the rate limiting step would take place at pH about 9.