147001-10-3

Upstream product

• 64-10-8 phenyl carbamate 
• 22711-23-5 4-chlorobenzil 
• 1889-78-7 2-bromo-1-(4-chlorophenyl)-2-phenylethanone 
• 43024-03-9 2-bromo-2-(4-chlorophenyl)-1-phenylethanone 
• 6332-83-8 2-(4-chlorophenyl)-1-phenylethanone 
• 1889-71-0 4'-chloro-2-phenylacetophenone 
• 108-90-7 chlorobenzene 
• 147000-93-9 5-(4-Chloro-phenyl)-1,4-diphenyl-1,3-dihydro-imidazol-2-one 
• 147000-96-2 4-(4-Chloro-phenyl)-1,5-diphenyl-1,3-dihydro-imidazol-2-one 
• 807309-02-0 α-amino-4-chloro-deoxybenzoin 
• 100542-67-4 α-amino-4'-chloro-deoxybenzoin 
• 147001-05-6 5-(p-Chlorphenyl)-5-hydroxy-1,4-diphenylimidazolin-2-on 

Relevant academic research and scientific papers

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).

Concerning the reaction mechanism of the hydantoin synthesis according to Biltz, I: Proof of the intermediates

The reaction mechanism of the rearrangement occurring during the hydantoin synthesis according to Biltz, proposed by Butler and Leitch, has been ascertained. The intermediate 3a, already proposed by Biltz, could be isolated out of the reaction mixture. Th