Methylamine → HCID 43351373, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence