Methanol → Acetic-formic anhydride

Participants

Reaction Conditions

Reaction Steps

Formic acetic anhydride was prepared by stirring a slurry of 34.4 g (0.42 mol) sodium formate in 35 mL ethyl ether and adding 24.9 mL (0.35 mol) of acetyl chloride dropwise keeping the temperature at 25° C. with intermittent cooling. After vigorous stirring for 5 hours the slurry was filtered into another reaction vessel and diluted with 100 mL CH2Cl2, then chilled to 0° C. A solution of 40 g (0.16 mol) 2-amino-N-(1,1-dimethylethyl)benzenemethanesulfonamide in 200 mL CH2Cl2 was then added dropwise keeping the temperature below 10° C. The mixture was then allowed to warm to room temperature and 50 mL methanol was added then stirred 18 hours. Evaporation of the solvent in vacuo left a residue that was taken up in chloroform, washed two times with NaHCO3 solution, dried (MgSO4) and stripped to dryness. The residue was triturated with n-butyl chloride and hexanes (1:1) and collected by filtration to afford 36.8 g of the title compound, m.p. 114°-115° C.

Provenance & Evidence