Triethylamine → 2-[2-(Pyridin-4-yl)ethyl]-1lambda~6~,2,6-thiadiazinane-1,1-dione

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Reaction Steps

A solution of sulphuryl chloride (7.5 g) in dichloromethane (20 cm3) was added dropwise over 15 minutes to a stirred solution of N-[2-(4-pyridyl)ethyl]-1,3-diaminopropane (10.0 g) in dichloromethane (100 cm3) and triethylamine (11.2 g) at -20°. The mixture was allowed to warm slowly to room temperature over 1 hour. After stirring for 16 hours the solution was filtered and sodium carbonate solution (50 cm3) was added. The aqueous phase was extracted with methylene chloride (2×50 cm3) and the dried (MgSO4) extracts were evaporated in vacuo to give an oil which was chromatographed on silica ("Merck 60. 9385") eluting with methanol:ethyl acetate, 1:19, to give a solid which was recrystallised from ethanol to afford 2-[2-(4-pyridyl)ethyl] tetrahydro-1,2,6-thiadiazine-1,1-dioxide, m.p. 124°-125° (2.0 g).

Provenance & Evidence