Chlorosuccinimide → HCID 86591859, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cyclopropylsulfonylamine tert-butyl carbamate (1.0 g, 4.52 mmol) dissolved in THF (10 mL) cooled to −78° C., was added n-BuLi (6.4 mL, 10.2 mmol, 1.6 M in hexane) and the reaction mixture was stirred for 1 h. To this solution was added a THF (10 mL) solution of NCS (0.86 g, 6.34 mmol). After stirred for 5 min, the bath was changed to ice bath and the mixture was stirred for 3 hrs at the temperature. The reaction mixture was diluted with ice water, the pH was adjusted to <4. The aqueous mixtire was extracted with EtOAc. The combined extracts were dried (MgSO4), concentrated and purified by flash chromatography over SiO2 using 0% to 60% EtOAc in hexanes as the eluent to afford 0.98 g (67%) of 1-chloro-cyclopropanesulfonamide-tert-butylcarbamate as a white solid: 1H NMR (500 MHz, CDCl3) δ ppm 1.51 (m, 11H), 2.01 (m, 2H), 7.60 (s, 1H).

Provenance & Evidence