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

Temperature

-20 °C

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).

1. temperatureto warm to rt
2. filtrationThe mixture was filtered
3. concentrationthe filtrate was concentrated in vacuo
4. dissolutionThe residue was dissolved in CH2Cl2 (2.0 L)
5. washThe resulting solution was washed with 1 N HCl (1.0 L), water (1.0 L), brine (1.0 L)
6. dry with materialdried over Na2SO4
7. filtrationIt was filtered
8. concentrationconcentrated in vacuo
9. customto give a slightly yellow solid which
10. customwas crystallized from hexane

ORD record

ord-d0b40db47cb94496872d613c4665e5af

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06878722B2