background and overview[1-2]
n-[4-(sulfonamide)phenyl]acrylamide (aspaa) monomer can be homopolymerized or copolymerized with other monomers to form pharmacologically active polymers that are water-soluble, have little toxic and side effects, and have slow large molecule drugs that release effects. at the same time, because the sulfonamide group has a certain alkali solubility, copolymers of aspaa and acrylic esters and other monomers can be used to prepare lithographic and computer-to-plate printing plates with good properties such as alkali developability, development latitude, and print durability.
preparation[1][3]
report 1,
add sulfonamide (1.00g) and pyridine (1.41ml) to 1,4-dioxane (30ml). acryloyl chloride (0.49 ml) was added dropwise and the solution was stirred at room temperature for 3 hours. 1m hcl was added and the solution was extracted with ethyl acetate. the extract was dried over brine and anhydrous sodium sulfate, and the solvent was removed to give a crude product that was pure enough for subsequent use.
report 2,
add 13.76g (80mmol) of p-aminobenzenesulfonamide, a certain amount of nahco3, 20mg of 1,3-dinitrobenzene, and 100ml of dmf into a dry three-necked flask. use ice for the reaction solution cool the bath to 0°c to 2°c, slowly add 7.96g (88mmol) of acryloyl chloride through a constant pressure dropping funnel while stirring, and react at a certain temperature for 3 hours after the dropwise addition is completed. filter to remove the salt, and pour the filtrate into 10 times the volume of methanol-water to precipitate a white solid. filter, wash the filter cake with water 3 to 5 times, and then recrystallize it with methanol to obtain aspaa. the yield is 50% to 65%, m.p. 234℃~ 236℃;1hnmrδ: 10.5 (s, 1h, conh), 7.83～7.85 (d, 2h, arh), 7.79～7.80 (d, 2h, arh), 7.29 (s, 2h, nh2), 5.81, 6.33 (m, 2h, =ch2), 6.47 (t, 1h, =ch); ir ν: 3342 (n-h), 3133, 3066 (=c-h), 1676 (c=o, amide i spectrum band), 1536 (conh, amide ii band), 1593, 1493 (-c=ch), 1411 (c-n stretching vibration), 1164 (so2-n), 836 (benzene ring disubstituted) cm-1 ;ana.lcalcd for c9h10n2o3s:c47.78, h4.45, n12.38; found c 47.12, h4.33, n12.21
references
[1]frompctint.appl., 2010065865, 10jun2010
[2] gao yingxin, bao yongzhong, huang zhiming, weng zhixue. reactivity rate of copolymerization of n-[4-(sulfonamide)phenyl]acrylamide with acrylonitrile and methyl methacrylate[j]. high acta molecule, 2004(03):450-453.
[3] gao yingxin, bao yongzhong, huang zhiming, weng zhixue. synthesis of n-[4-(sulfonamide)phenyl](meth)acrylamide [j]. synthetic chemistry, 2005(01):22- 24+36-1.
