Tert-Butylamine → N-tert-butyl-3-chloropropane-1-sulfonamide

Participants

Reaction Conditions

Reaction Steps

Step Ia) A neat solution of tert-Butylamine (315.3 mL, 3.0 mol) was dissolved in THF (2.5 L), cooled to −20° C., and 3-Chloropropanesulfonyl chloride (182.4 mL, 1.5 mol) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 24 h. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in CH2Cl2 (2.0 L). The resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L) and dried over Na2SO4. It was filtered and concentrated in vacuo to give a slightly yellow solid which was crystallized from hexane to afford the product as a white solid (316.0 g, 99%): 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (bs, 1H).

Provenance & Evidence