Preparation of Ethenesulfonamide¹

Abstract

ETHENESULFONAMIDE 729An analytical sample was obtained by crystallization of the crude material from benzene followed by 3 recrystallizations from ethyl acetate. It softened at 150°and melted at 192.5-194.0°.A mixed melting point of 2-quinoxalinoformamide and 2acetamidoquinoxaline (m.p. 192.6-193.8°)12 showed a sharp depression.3',4'-Dichloroformanilide. Acetic formic anhydride was prepared from acetic anhydride (40.8 ml.) and 98% formic acid (17.2 ml.). This mixture was cooled in an ice bath to 12°. A gradual addition of 3,4-dichloroaniline (32.4 g., 0.2 mole) was made so that the temperature did not rise above 40°. The dark red solution was held at room temperature (35°) for five hours after which ether (100 ml.) was added. The following day the dark purple solution was extracted with 2 X 100 ml. of water. The ether layer was evaporated on the steam bath to furnish 36.7 g. (96.5%) of crude material, m.p. 94-103°. A hot benzene (150 ml.) solution of the crude product was treated with Nuchar C. The filtrate was cooled for several hours prior to collecting the product by filtration. A cold benzene wash was applied to the gray solid. The purified 3',4'-dichloroformanilide weighed 30.4 g. It sintered at 99°and melted at 110-112°. Recrystallization from a large volume of carbon tetrachloride furnished off-white crystals with no change in melting point. The product is soluble in chloroform and cyclohexene but insoluble in petroleum ether or cyclohexane. Possibly a reduction in the quantity of acetic formic anhydride to slightly over one mole would give a satisfactory result for this type of preparation. Skokie, III.

Inhibition of the Antibacterial Target UDP-(3-O-acyl)-N-acetylglucosamine Deacetylase (LpxC): Isoxazoline Zinc Amidase Inhibitors Bearing Diverse Metal Binding Groups

“…Chloro-oxime 3 was generated in situ from 0.33 mmol (50 mg) of p -anisaldehyde oxime and N -chlorosuccinimide (44 mg, 0.33 mmol) as described in the synthesis of 6 . Vinyl sulfonamide (43 mg, 0.4× mmol) was added as a solution in CH 2 Cl 2 (10 mL). N -Methyl morpholine (44 μL, 0.33 mmol) was added, and the solution was stirred for 2 h. The solution was concentrated and partitioned between EtOAc and water.…”

Polymers from S-vinyl monomers: reactivities and properties

“…The radical homopolymerization of vinyl sulfonamides with an unsubstituted amide is generally described to be difficult, and the lead only to polymers of low molar mass. 189 However, specific substituents attached to the nitrogen have been found to tremendously impact the polymerization behavior and to substantially improve it as well in some cases. For example N -allyl vinyl sulfonamides can be polymerized using radical initiators 190 while many alkyl vinyl sulfonamides cannot be polymerized under these conditions.…”

Symmetrical Tertiary Amines: Applications and Synthetic Approaches

“…In 1958 Matlack reported the tertiary amine preparation from the ethylenesulfonamide derivatives (Scheme 16). [ 88 ]…”