Sodium Methoxide → HCID 21282824, compound

Participants

Reaction Steps

Methyl 3-methyl-2-((((1-methylethyl)amino)-sulfonyl)amino)benzoate (19.9 grams; 0.07 mole) and sodium methylate (7.5 grams; 0.14 mole) were mixed with 200 ml. of methanol and the resulting mixture heated at the reflux temperature thereof for a period of about 4 hours. The reaction mixture was then cooled and the methanol removed in vacuo. The resulting residue was dissolved in 200 ml. of water and the resulting solution extracted with 100 ml. of ether. The aqueous layer was then separated and acidified to a pH of about 2.0 with concentrated hydrochloric acid. The resulting precipitate formed upon acidification was recovered by filtration, dried and recrystallized from cyclohexane. As a result of these operations, the desired 8-methyl-3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide compound was obtained as a crystalline solid having a melting point of 126.5°-127.5° C. and having carbon, hydrogen and nitrogen contents of 51.70, 5.63 and 11.15 percent, respectively, as compared with the theoretical contents of 51.93, 5.51 and 11.02 percent, respectively, calculated for the named structure.

Provenance & Evidence