70469-40-8

Basic information

• Product Name: benzyl 5-methyl-4-oxo-2-thioxoimidazolidine-1-carboxylate
• Synonyms: benzyl 5-methyl-4-oxo-2-thioxoimidazolidine-1-carboxylate
• CAS NO: 70469-40-8
• Molecular Weight: 264.305
• Mol File: 70469-40-8.mol

Chemical Properties

• CAS DataBase Reference: benzyl 5-methyl-4-oxo-2-thioxoimidazolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 5-methyl-4-oxo-2-thioxoimidazolidine-1-carboxylate(70469-40-8)
• EPA Substance Registry System: benzyl 5-methyl-4-oxo-2-thioxoimidazolidine-1-carboxylate(70469-40-8)

Safety Data

• Hazardous Substances Data: 70469-40-8(Hazardous Substances Data)

Upstream product

• 4132-86-9 N-benzyloxycarbonylalanine 
• 16182-04-0 Ethoxycarbonyl isothiocyanate 

Relevant articles and documents

Enantioselective Synthesis of 5,5-Disubstituted Hydantoins by Br?nsted Base/H-Bond Catalyst Assisted Michael Reactions of a Design Template

A new method for the enantioselective synthesis of 5,5-disubstituted (quaternary) hydantoins was developed on the basis of an organocatalytic Michael reaction approach involving the use of 2-benzylthio-3,5-dihydroimidazol-4-ones as key hydantoin surrogates. The method is general with respect to the substitution pattern at the hydantoin N1 (alkyl, aryl, acyl), N3 (aryl), and C5 (linear/branched alkyl, aryl) positions and affords essentially single diastereomeric products with enantioselectivities higher than 95 % ee in most cases. Among the bifunctional Br?nsted base/H-bond catalysts examined, a known squaramide–tertiary amine catalyst and a newly prepared squaramide–tertiary amine catalyst provide the highest selectivity so far with either nitroolefins or vinyl ketones as the acceptor components. Kinetic measurements support a first-order rate dependence on both reaction partners, the donor template and the Michael acceptor, whereas competitive 1H NMR spectroscopy experiments reveal the high ability of the template for catalyst binding.