Cesium carbonate → N-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-1,1-dioxo-1,2-benzothiazol-3-amine

Participants

Reaction Conditions

Reaction Steps

182 mg of 1,2-benzisothiazol-3-amine 1,1-dioxide and 326 mg of cesium carbonate are added to 386 mg of 1-[bis(4-chlorophenyl)methyl]azetidin-3-yl methylsulfonate in solution in 10 cm3 of dimethylformamide. The reaction medium is then stirred at 100° C. for 9 hours and then concentrated under reduced pressure (2.7 kPa). The residue is washed four times with 5 cm3 of boiling distilled water, disintegrated by stirring in 5 cm3 of distilled water at room temperature and then recovered by filtration and purified by flash chromatography on silica gel [eluent: dichloromethane/methanol (98/2 by volume)]. 53 mg of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(1,1-dioxo-1H-1λ6-benzo[d]isothiazol-3-yl)amine are obtained in the form of a pasty product [[1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 3.17 (mt: 2H); 3.61 (broad t, J=7.5 Hz: 2H); 4.37 (s: 1H); 4.75 (mt: 1H); from 6.30 to 6.40 (unresolved complex: 1H); from 7.20 to 7.35 (mt: 8H); 7.62 (broad d, J=7.5 Hz: 1H); 7.69 (broad t, J=7.5 Hz: 1H); 7.76 (broad t, J=7.5 Hz: 1H); 7.93 (broad d, J=7.5 Hz: 1H)].

Provenance & Evidence