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

Temperature

-20 °C

tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to −20° C. and treated slowly with 3-chloropropanesulfonyl chloride (1.5 mol, 182.4 mL). The reaction mixture was warmed to room temperature and stirred for 24 hours. The mixture was filtered, and the filtrate was concentrated in vacuo. The concentrate was dissolved in dichloromethane (2.0 L), washed with 1N HCl (1.0 L), water (1.0 L), brine (1.0 L), dried over Na2SO4, filtered, and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to provide the desired 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. temperatureThe reaction mixture was warmed to room temperature
2. filtrationThe mixture was filtered
3. concentrationthe filtrate was concentrated in vacuo
4. dissolutionThe concentrate was dissolved in dichloromethane (2.0 L)
5. washwashed with 1N HCl (1.0 L), water (1.0 L), brine (1.0 L)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give a slightly yellow solid, which
10. customwas crystallized from hexane

ORD record

ord-63bf7affcbaa4b2ba172a57e141a1983

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935670B2