4-Toluenesulfonyl chloride → 2,2-Dimethyl-1-(toluene-4-sulfonyl)-aziridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,2-dimethylaziridine (5.42 g; 0.076 mole; sold by Polysciences, Inc., Warrington, PA) in pyridine (100 mL) cooled in an ice bath, is added p-toluenesulfonyl chloride (21.81 g; 0.114 mole) in one portion. The reaction is stirred at 0° C. for 2 hours; diluted with ether (400 mL); washed with cold 10% H3PO4 (2×150 mL), with a saturated NaHCO3 solution (3×150 mL) and brine (1×150 mL); and dried over MgSO4. Rotary evaporation of the solution affords a yellowish solid which is crystallized from ethyl acetate to yield the product 2,2-dimethyl-N-p-toluenesulfonyl-aziridine (4.48 g). 1H NMR (CDCl3):1.53 (6H, s), 2.45 (5H, m), 7.2-8.0 ppm (4H, m, aromatics).

Provenance & Evidence