Triethylamine → HCID 61248038, compound

To a cold (0° C.) solution of aminoacetaldehyde dimethyl acetal (2.22 mL, 20.4 mmol) and triethylamine (3.54 mL, 25.4 mmol) in dichloromethane (60 mL) was added 3-chloropropanesulfonyl chloride (2.06 mL, 16.9 mmol) in dichloromethane (40 mL) dropwise. The reaction mixture was warmed to room temperature and stirred one hour. The reaction mixture was quenched with water. The organic phase was washed with water and brine, then dried over sodium sulfate. Filtration and concentration, followed by trituration with ether provided N-[2,2-bis(methyloxy)ethyl]-3-chloro-1-propanesulfonamide as a white solid. 1H NMR (400 MHz, CDCl3) δ 4.56 (s, 1 H), 4.42 (t, J=5.0 Hz, 1 H), 3.68 (t, J=6.1 Hz, 2 H), 3.42 (s, 6 H), 3.25-3.21 (m, 4 H), 2.28 (m, 2 H).

1. customThe reaction mixture was quenched with water
2. washThe organic phase was washed with water and brine
3. dry with materialdried over sodium sulfate
4. filtrationFiltration and concentration

ORD record

ord-92373f6fd20846768904de63308bda44

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691991B2