Chlorosuccinimide → 1-(3-chlorotetrahydro-2H-1,3-thiazin-2-ylidene)-3-(2,4-dichlorophenoxy)-1-nitro-2-propanone

Participants

Reaction Steps

3.6 g of 1 and 2.1 g of N-chlorosuccinimide were combined in 150 ml of carbon tetrachloride and the mixture was refluxed for 1 hour. The resulting mixture was filtered through Celite and the solvent was evaporated to give a liquid, which was triturated in ether, decolorized with activated charcoal and filtered through Celite and stripped of solvent to give a yellow cloudy liquid. This was passed through Florisil, using methylene chloride as eluent; then stripped to give an oil, which was kept in a refrigerator over a week-end. Part of the oil crystallized. On scratching, more crystals formed. Separation of the crystals gave 2, as bright yellow crystals, m.p. 103°-105°.

Provenance & Evidence