Benzenesulfonyl chloride → HCID 20335988, compound

Participants

Reaction Steps

A stirred suspension of 40 g. (1.02 mole) of sodamide in dry toluene was treated dropwise with 116 g. (1.0 mole) of 1,2-dimethyl-4-pyrazolidinol at 80° C. After 4.5 hrs. at reflux the mixture was cooled and maintained below 20° C. while 161.0 g. (1.0 mole) of benzenesulfonyl chloride was added dropwise. After stirring 1.0 hr. the reaction mixture was shaken with dilute sodium hydroxide, the separated toluene layer dried over sodium sulfate and concentrated at reduced pressure. The residue was dissolved in 300 ml. of aniline, the mixture heated 2.5 hrs. on the steam bath and refluxed for 3.0 hrs. The cooled mixture was extracted with dilute sodium hydroxide solution and the separated aqueous layer extracted with isopropyl ether. The combined organic layers after drying over sodium sulfate were concentrated and the residue distilled to a pot temperature of 140° C./80 mm. The residue which would not crystallize was distilled at 110°-125° C./0.1 mm. to give 86 g. of product.

Provenance & Evidence