Triethylamine → (Methylsulfonyl)-carbamic acid ethyl ester

To a mixture of methanesulfonamide (1.0 g, 11 mmol), triethylamine (1.9 mL, 14 mmol), and DMAP (0.13 g, 1.1 mmol) in DCM (20 mL) cooled in an ice-water bath was added ethyl carbonochloridate (1.1 mL, 12 mmol) dropwise via a syringe under an argon atmosphere. The mixture was allowed to warm up to rt overnight. The reaction mixture was concentrated, and the residue obtained was dissolved in EtOAc (100 mL). The solution was washed with 1 N HCl (20 mL) and brine, and dried over MgSO4. The mixture was filtered and concentrated to give compound 12a as a yellow oil. 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.86 (br. s., 1H), 4.28 (q, J=7.25 Hz, 2H), 3.30 (s, 3H), 1.33 (t, J=7.25 Hz, 3H).

1. temperaturecooled in an ice-water bath
2. concentrationThe reaction mixture was concentrated
3. customthe residue obtained
4. washThe solution was washed with 1 N HCl (20 mL) and brine
5. dry with materialdried over MgSO4
6. filtrationThe mixture was filtered
7. concentrationconcentrated

ORD record

ord-8f0d9d82708642078e53390089a88bcc

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193736B2