Morpholine → 1,4-Bis(morpholinothio)benzene

Participants

Reaction Steps

47 g (0.334 mol) of 1,4-benzene dithiol was made into a 30% benzene solution, and then the resulting solution was added dropwise to a solution of 91 g (0.674 mol) of N-chlorosuccinimide in 300 cc of anhydrous benzene at a temperature below 10°C. The resulting sulfenylchloride solution was separated from the by-produced succinimide and 118 g (0.674 mol) of morpholine was added dropwise thereto at a temperature below 10°C. The by-produced morpholine hydrochloride was filtered off and the filtrate was distilled to remove benzene, by which a crude crystal of 1,4-bis(morpholinothio)benzene was obtained. This crude crystal was recrystallized and purified from ethanol. The purified crystal had a melting point of 95°C, and the yield was 70%. It was identified from NMR, IR and elementary analysis that the crystal is 1,4-bis(morpholinothio)benzene.

Provenance & Evidence