Dichloromethane → Halofenozide

Participants

Reaction Conditions

Reaction Steps

To a 5 L round bottom flask, equipped with a mechanical stirrer, containing the 571 g of wet N'-tert-butyl-N-(4-chlorobenzoyl)hydrazine intermediate and equipped with a 500 mL addition funnel containing 371 g of benzoyl chloride, is charged 1500 mL of methylene chloride, 250 mL of water and lastly 223 g of 50% by weight aqueous sodium hydroxide. The flask contents are stirred and cooled to 5° C. and the benzoyl chloride is added dropwise during a one hour period so that the temperature of the flask contents does not exceed 10° C. After allowing the flask contents to warm to room temperature, stirring is stopped and the organic and aqueous phases are allowed to separate overnight. The upper aqueous phase is removed by suction and is replaced by 500 mL of fresh water, the heterogeneous mixture is stirred, the phases are allowed to separate and the upper aqueous phase again is removed by suction. This washing procedure is repeated two more times and then 500-800 mL of hexane is added to the organic remainder. The contents are briefly stirred and then are poured onto a glass flitted Buchner funnel. The filter cake is washed extensively with a total of 2 L of hexane followed by 10 L of water and then is dried in vacuo at 65° C. for two days to give 758.2 g of N'-tert-butyl-N-(4-chlorobenzoyl)-N'-benzoylhydrazine as a white powder melting at 197°-198° C.

Provenance & Evidence