Ethyl xanthate → 3-chloro-N-hydroxy-2,2-dimethylpropanamide

Participants

Reaction Steps

A two liter resin kettle was equipped with two inlet tubes, a thermometer, stirring paddle, pH probes and a cooling jacket. A solution of hydroxylamine sulfate (264 g, 1.61 moles) and ethyl xanthic acid, potassium salt (0.5 g, 0.003 mole) in 700 ml of water was added to the kettle and the stirrer started. One of the inlet tubes was connected through a metering pump to a reservoir containing an aqueous 50% sodium hydroxide solution. The addition of base to the reaction mixture was regulated by an electronic pH meter/controller connected to the pump and pH probe and set for pH of 7.2. Aqueous base was delivered to the reactor until that pH was attained. The other inlet tube was connected through a metering pump to a reservoir containing 3-chloro-2,2-dimethylpropionyl chloride (286 g, 1.84 moles). The acid chloride was added to the reaction mixture during a period of 2.5 hours at a temperatue of 28° C., maintaining a pH of 7.2 by simultaneous addition of base. The reaction slurry was then vacuum filtered and the filter cake dried. The dried filter cake weighted 293 g. An aliquot of the filter cake was dissolved in a mixture of DMF and toluene. Analysis of the extract using GLPC indicated the yield of 3-chloro-N-hydroxy-2,2-dimethylpropanamide, based on the amount of 3-chloro-2,2-dimethylpropionyl chloride, was 85%.

Provenance & Evidence