2-Methoxyethane-1-sulfonaMide synthesis

Yield:51517-04-5 46%

Reaction Conditions:

with ammonium hydroxide in water at 20; for 3 h;

Steps:

37.1 Step 1

In water (16 mL) was suspended 1-bromo-2-methoxyethane (2.00 mL, 21.3 mmol). Sodium sulfite (2.95 g, 23.4 mmol) was added and the mixture was refluxed for 24 hours. The solvent in the reaction mixture was evaporated under reduced pressure and the residue was purified by slurrying in chloroform to give a white solid (6.11 g). To the white solid were added thionyl chloride (15.5 mL, 213 mmol) and DMF (0.082 mL, 1.06 mmol) and the mixture was stirred at 100° C. for 3 hours. The solvent in the reaction mixture was evaporated under reduced pressure. Chloroform was added, insoluble substance was filtered off, and the solvent in the filtrate was evaporated under reduced pressure. A 25% aqueous ammonia solution (10 mL) was added to the resulting residue and the mixture was stirred at room temperature for 3 hours. The solvent in the reaction mixture was evaporated under reduced pressure. Chloroform was added, insoluble substance was filtered off, and the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7) to give 2-methoxyethanesulfonamide (1.36 g, 460 yield).

References:

US2013/65905,2013,A1 Location in patent:Paragraph 0234