Methylamine → HCID 43351373, compound

Temperature

0 °C

A solution of 3-bromomethyl-benzonitrile (2 g, 10.2 mmol) in EtOH (50 mL) is treated with a solution of Na2SO3 (1.3 g, 10.3 mmol) in H2O (50 mL) and heated at reflux for 4 hours. The mixture is concentrated in vacuo. The residue is suspended in DCM (100 mL) and DMF (1 mL), cooled to 0° C. and treated with oxalyl chloride (8 mL, 43.4 mmol). The mixture is warmed to room temperature and stirred for 3 hours. The mixture is diluted with brine, extracted with DCM (2×100 mL), dried with Na2SO4, filtered, and concentrated in vacuo. The residue is dissolved in THF (25 mL), methylamine (2 M, 12.5 mL, 25 mmol) is added and the mixture is stirred for 12 hours. The mixture is diluted with EtOAc (100 mL), washed with saturated aqueous NH4Cl (2×100 mL), dried with Na2SO4, filtered, and concentrated in vacuo. The residue is purified by flash chromatography eluting with 20%-80% EtOAc/heptane to afford C-(3-cyano-phenyl)-N-methyl-methanesulfonamide (1.5 g, 69%) as a powder. MS: 209 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 2.60 (d, J=4.8 Hz, 3H), 4.44 (s, 2H), 7.02 (m, 1H), 7.61 (m, 1H), 7.74 (m, 1H), 7.85 (m, 2H).

1. temperatureheated
2. temperatureat reflux for 4 hours
3. concentrationThe mixture is concentrated in vacuo
4. temperatureThe mixture is warmed to room temperature
5. extractionextracted with DCM (2×100 mL)
6. dry with materialdried with Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. dissolutionThe residue is dissolved in THF (25 mL)
10. stirringthe mixture is stirred for 12 hours
11. washwashed with saturated aqueous NH4Cl (2×100 mL)
12. dry with materialdried with Na2SO4
13. filtrationfiltered
14. concentrationconcentrated in vacuo
15. customThe residue is purified by flash chromatography
16. washeluting with 20%-80% EtOAc/heptane

ORD record

ord-0de2cfdf5fb0487cb0921be340452f46

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202863B2