17816-50-1

Upstream product

• 22711-21-3 4-methoxybenzil 
• 57-13-6 urea 
• 100-66-3 methoxybenzene 
• 1023-17-2 4-methoxyphenyl benzyl ketone 
• 1889-77-6 2-bromo-1-(4-methoxy-phenyl)-2-phenyl-ethanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 4254-17-5 4-methoxybenzoin 
• 611-94-9 4-Methoxybenzophenone 
• 151-50-8 potassium cyanide 

Downstream Products

• 54833-61-3 R,S-5-(p-Methoxyphenyl)-3-methyl-5-phenylhydantoin 
• 56079-80-2 3-<3-(4-phenyl-1-piperidyl)propyl>-5-(4-methoxyphenyl)-5-phenylhydantoin hydrochloride 
• 57496-20-5 4'-(S)-hydroxyphenytoin 
• 2784-27-2 5-(4-hydroxyphenyl)-5-phenylhydantoin 

Relevant academic research and scientific papers

Synthesis of glycoluril catalyzed by potassium hydroxide under ultrasound irradiation

Synthesis of the glycolurils catalyzed by potassium hydroxide was carried out in 17-75% yield at 40 °C in EtOH under ultrasound irradiation. Compared to the method using stirring, the main advantage of the present procedure is milder conditions and shorter reaction time.

Ultrasound-enhanced green synthesis of 5,5-diphenylhydantoin derivatives using symmetrical or unsymmetrical benzils

A rapid, highly efficient and mild green synthesis of 5,5-diphenylhydantoin derivatives was achieved from the reaction of symmetrical or unsymmetrical benzil derivatives with urea in the presence of ethanolic KOH under ultrasound irradiation. This simple method affords 5,5-diphenylhydantoin derivatives at room temperature in short reaction time with high yield and purity. This study aimed to overcome the limitations and drawbacks of the reported methods such as tedious work-up, low yield and long reaction time.

One-pot synthesis of phenytoin analogs

A series of phenytoin analogs (5,5-diphenylimidazolidine-2,4-dione or 5,5-diphenyl-hydantoin) were synthesized in 65-75% yield from the corresponding substituted benzils. The same products were also obtained directly from α-hydroxy ketones via one-pot procedure.

Concerning the reaction mechanism of the hydantoin synthesis according to Biltz, II: Influence of substituents on the direction of the rearrangement

From 1-13C-labelled 4-monosubstituted benzils 1a-c and the ureas 3a-d the 5-aryl-5-phenylhydantoines 6a-c and the 3-substituted 5-aryl-5-phenylhydantoines 9a-i were obtaincd as mixtures of isotopomeres. The distribution of 13C-labelling of C-4 and C-5 was determined by mass- and 13C-nmr-spectroscopy. As in the case of benzilic acid rearrangement the a-methylphenyl- and 4-methoxyphenyl-increment, respectively, migrate less easily than does the unsubstituted phenyl group, which in turn migrates less easily than the 4-chlorophenylrest. In the latter case the differences are small and in one example cven slightly reversed. The characteristics of the rearrangement is explained by thermodynamic control of the reaction by preceding equilibria (Schemes 2 and 3).