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. 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 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. The mixture was filtered and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to provide 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 (b, 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 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. filtrationThe mixture was filtered
8. concentrationconcentrated in vacuo
9. customto give a slightly yellow solid, which
10. customwas crystallized from hexane

ORD record

ord-ab1b1c9beaf440c3bc56147f847450ad

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601686B2