Study On The Synthesis Of Cyclopropanesulfonamide

Cyclopropanesulfonamide is an important intermediate. In this paper, the synthesis of cyclopropanesulfonamide was researched from Allyl alcohol via 7 steps, including sulfonation, chloration, esterification, cyclization, hydrolysis, chloration and amination, the overall yield is up to 61%.The optimum condition of each reaction has been obtained through one-factor and orthogonal experiment in the synthetic process. Then, the optimum of sodium 3-hydroxypropanesulfonate:mC3H6O:VH2O=1:7, reaction temperature 85℃, reaction time 8.0h, the yield is up to 98%; The optimum of 3-chloropropanesulfonyl chloride:solvent 1,2-dichloroethane,VC2H4Cl2:mC3H5KO3S=7:1, the yield is up to 95.9%, the purity is up to 91.3%; The optimum of isopropyl 3-chloropropanesulfonate:reaction temperature -5～0℃, nC3H6Cl2O2S:nC6H15N=1:1.3, reaction time 2h, mC3H6Cl2O2S:VCH2Cl2=1:2, the yield is up to 98%, the purity is up to 91.9%; The optimum of isopropyl cyclopropanesulfonate:reaction temperature -5～0℃, nC6H13ClO3S:nC4H9KO=1:1.3, reaction time 4h, mC6H13ClO3S:VC4H8O= 1:1.25, the yield is up to 93.7%, the purity is up to 98.1%; The optimum of cyclopropanesulfonic acid, potassium salt:solvent water, VH2O:mC6H12O3S=4:1, the yield is up to 93%; The optimum of cyclopropanesulfonyl chloride:solvent 1,2-dichloroethane, VC2H4Cl2: mC3H5KO3S=7:1, the yield is up to 96.9%, the purity is up to 99.2%; The optimum of cyclopropanesulfonamide:cyclopropanesulfonyl chloride is not treated and react with amine directly, the yield is up to 95.7%, the purity is up to 99.8%. This method is of grand economic worth for the future industry production due to its advantages of rich raw material, low cost, high yield and little harm to nature environment.The structures of intermediates and product were confirmed by GC、GC-MS and 1H-NMR.