Nitrogen → 2-Propenamide, 2-methyl-N-(4-(phenylamino)phenyl)-

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A one liter flask equipped with an agitator was charged with 90 grams of methanol and 30 grams (0.55 mol) of sodium methoxide while under a slow N2 purge. The mixture was stirred until solution was achieved. 450 milliliters of xylene followed by 92 grams (0.5 mol) of p-aminodiphenylamine and 70.8 (0.71 mol) of methylmethacrylate were added to the flask while agitating. The homogeneous solution was then slowly heated and methanol was removed through a packed column. Methanol forms an azeotrope with methylmethacrylate and thus the distillate contained some methylmethacrylate as well as some xylene. Approximately 120 grams of distillate was removed over a period of two hours, during which the column outlet temperature stayed at 62°-63° C. while the flask temperature rose from 90° C. to 138° C. The column outlet temperature then started climbing, indicating the absence of methanol. The flask was then cooled to 70° C. and the sodium salt was filtered through a Buchner funnel. The salt was first washed with xylene to remove the residual amine and then with hexane. The salt was allowed to air dry and then restirred in one liter of cold water. It was then hydrolyzed with 10 percent sulfuric acid to pH of about 6. The product was filtered and air dried yielding 101 grams of N-(4-anilinophenyl) methacrylamide having a melting point of 102°-103° C. The yield was 80.15 percent.

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