Cysteamine Hydrochloride → 2-[(4-Methyl-1,2,5-oxadiazol-3-yl)methylthio]ethylamine
Reaction equation
O[CH2:2][C:3]1[C:7]([CH3:8])=[N:6][O:5][N:4]=1.Cl.[NH2:10][CH2:11][CH2:12][SH:13]>Br>[CH3:8][C:7]1[C:3]([CH2:2][S:13][CH2:12][CH2:11][NH2:10])=[N:4][O:5][N:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-hydroxymethyl-4-methylfurazan (2.49 g; 21.8 mmoles) [prepared in Step A] and 2-aminoethanethiol hydrochloride (2.48 g; 21.8 mmoles) in 60 ml of 48% aqueous hydrobromic acid was stirred and heated at reflux temperature for 23 hours and then at ambient temperature for 40 hours. The excess hydrobromic acid was removed under reduced pressure, and the oil residue was dissolved in isopropyl alcohol, filtered through Celite and the product was crystallized from the filtrate. Recrystallization from isopropyl alcohol yielded the title compound as the hydrobromide salt, mp 142°-143°.