Methanol → HCID 1477336, compound

Participants

Reaction Steps

To a stirring solution of methyl-2-aminothiophene carboxylate (10 g) in CH2Cl2 (350 ml) at 0° C. is added triethylamine (13.51 g). Methanesulfonyl chloride (15.28 g) is then added dropwise at 0° C. over 15 min. The mixture is stirred for 16 h allowing the solution to warm to ambient temperature. The organic layer is washed with water (100 ml) and dried over MgSO4. The solvent is removed in vacuo to afford a crude residue. This material is dissolved in MeOH (400 ml) and a solution of NaOMe in methanol is added (2.92 g Na metal in 150 ml MeOH) at ambient temperature. The resulting heterogeneous mixture is stirred at ambient temperature overnight. The mixture is concentrated to approximately 150 mL volume, cooled to 0° C., and filtered to afford 14.5 g (88%) of the title compound as a tan solid (Na salt). Physical characteristics: 1H NMR (DMSO-d6) δ 2.68, 3.61, 6.23, 6.91; IR (diffuse reflectance) 1683, 1507, 1464, 1316, 1248, 1233, 1222, 1190, 1150, 1124, 1075, 979, 787, 763, 685 cm−1; MS (CI) m/z 258 (MH+).

Provenance & Evidence