908343-65-7

Basic information

• Product Name: (4S,5R)-cis-3-methylamino-4-methyl-5-phenylthiazolidine-2-thione
• Synonyms: (4S,5R)-cis-3-methylamino-4-methyl-5-phenylthiazolidine-2-thione
• CAS NO: 908343-65-7
• Molecular Weight: 223.363
• Mol File: 908343-65-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (4S,5R)-cis-3-methylamino-4-methyl-5-phenylthiazolidine-2-thione(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-cis-3-methylamino-4-methyl-5-phenylthiazolidine-2-thione(908343-65-7)
• EPA Substance Registry System: (4S,5R)-cis-3-methylamino-4-methyl-5-phenylthiazolidine-2-thione(908343-65-7)

Safety Data

• Hazardous Substances Data: 908343-65-7(Hazardous Substances Data)

Upstream product

• 75-15-0 carbon disulfide 
• 13148-28-2 (+)-(2S,3S)-trans-1,2-dimethyl-3-phenylaziridine 
• 94133-42-3 (+)-Chloroephedine hydrochloride 
• 50-98-6 ephedrine hydrochloride 
• 124919-00-2 (-)cis-(2S:3R)-N-Methyl-2-methyl-3-phenylaziridin 
• 299-42-3 ephedrine 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 47497-54-1 bis-((1R,2S)-2-dimethylamino-1-phenyl-1-propyl) disulfide 
• 942-49-4 (1R,2S)-N-methylthiolephedirine 

Relevant articles and documents

Efficient synthesis of cis-thiazolidinethiones derived from ephedrines

The reaction of chlorodeoxypseudoephedrine or chlorodeoxynorpseudoephedrine hydrochlorides with sodium dithiocarbonate in stirring ethanol at 0 °C to stereoselectively afford the corresponding cis-thiazolidinethiones in good yields (81% and 95%) is reported. The in situ formation of a cis-aziridine to explain the presence of trans-thiazolidinethione as a side product is proposed when the same reaction was carried out at room temperature. In addition, a 70:30 mixture of trans-isomers of a thiazolidinethione/isothiazolidinethione was formed when a cis-aziridine NH was reacted with carbon disulfide in refluxing ethanol. The analogous reaction with cis-aziridine N-Me stereoselectively affords the corresponding cis-thiazolidinethione. The 1H and 13C NMR data of the thiazolidinethiones were assigned. cis-3,4-Dimethyl-5-phenylthiazolidine-2-thione was crystallized from ethanol and its X-ray diffraction structure was analyzed.

ENANTIOMERICALLY PURE β-AMINO SULFIDES AND β-AMINO THIOLS FROM EPHEDRINE

Ephedrine and pseudoephedrine are converted by means of a Mitsunobu reaction to respectively trans- and cis-aziridines, which can be ring-opened at the benzylic center with inversion of configuration by thiols and thiol acids.The trans-aziridine from ephe