Trichloromethanesulfenyl chloride → HCID 13326271, compound

Participants

Reaction Steps

To a mixture of 6-cyano-1-(2,6-dimethylanilino)-2,4-pyrimidinedione (50 mmol) and aqueous sodium hydroxide (50 mmol) is added 55 mmol of trichloromethylsulfenyl chloride in methylene chloride at 5° and with rapid stirring. When the pH of the mixture is 7-8, the reaction is complete. The layers are separated and the aqueous phase is discarded. The methylene chloride is removed, followed by washing with water and drying to yield a mixture of two crude products. Separation by chromatography on silica gel, eluting with acetone/hexane, gives the two final products, 6-cyano-1-(2,6-dimethylanilino)-3-trichloromethylthio-2,4-pyrimidinedione and 6-cyano-1-(2,6-dimethyl-N-trichloromethylthioanilino)-2,4-pyrimidinedione.

Provenance & Evidence