908343-65-7

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

1,3-Heterazolidines-2-heterounsaturated compounds derived from ephedrines

Herein, a direct and easy method for preparing 2-oxo-, 2-thione- or 2-imine-1,3-heterazolidines derived from ephedrines and norephedrines are reported. The method is based on solvent free heating of ephedrines with oxocyanate or thiocyanate salts (180-200 °C). In the reactions with potassium oxocyanate in refluxing ethanol, it was possible to isolate ureidic derivatives. The structure and stereochemistry of the compounds were determined by 1H, 13C NMR, IR spectroscopies and mass spectrometry. Ureidic derivatives, cis-1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one are new compounds. Ephedrineurea, cis-1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one were also studied by X-ray diffraction.

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