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To a solution of 0.274 ml (0.347 g, 0.0046 mole) of carbon disulfide in 20 ml of ethanol was added 0.80 ml (0.80 g, 0.0091 mole) of morpholine. A white mixture resulted. The mixture was heated to reflux and a solution of 1.0 g (0.0038 mole) of S-t-butyl S-chloromethyl ethylphosphonotrithioate in 3 ml at ethanol was added. (The S-t-butyl S-chloromethyl ethylphosphonotrithioate was prepared according to the procedure of Example I, steps (a) and (b), from ethylthionophosphine sulfide, t-butyl mercaptan, triethylamine, and bromochloromethane.) The mixture was refluxed for 16 hours. After cooling, 20 ml of water was added and the mixture was twice extracted with ether. The ethereal solution was washed with 20 ml of water and 20 ml of brine, dried with magnesium sulfate, and evaporated to a viscous oil. Purification by a preparative, centrifugally accelerated, thin-layer (4 mm, silica gel) chromatograph, with 9:1 hexane-acetone as eluent, afforded 0.39 g (28% of theoretical yield) of the title compound, a clear, viscous oil. The structure was confirmed by nuclear magnetic resonance, infrared and mass spectroscopy.

1. customA white mixture resulted
2. temperatureThe mixture was heated
3. temperatureto reflux
4. temperature) The mixture was refluxed for 16 hours
5. temperatureAfter cooling
6. extractionthe mixture was twice extracted with ether
7. washThe ethereal solution was washed with 20 ml of water and 20 ml of brine
8. dry with materialdried with magnesium sulfate
9. customevaporated to a viscous oil
10. customPurification by a preparative,
11. customthin-layer (4 mm, silica gel) chromatograph, with 9:1 hexane-acetone as eluent, afforded