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

Temperature

-20 °C

25 tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to −20° C. 3-Chloropropanesulfonyl chloride (1.5 mol, 182.4 mL) was added slowly. The reaction mixture was allowed to warm to room temperature and stirred for 24 hours. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in dichloromethane (2.0 L). The resulting solution was washed with 1N 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 (br, 1H).

1. temperatureto warm to room temperature
2. filtrationThe mixture was filtered
3. concentrationthe filtrate was concentrated in vacuo
4. dissolutionThe residue was dissolved in dichloromethane (2.0 L)
5. washThe resulting solution was washed with 1N 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-a964d0aea88843fa9635f5a83b18d7f8

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592336B2