[N:1]#[C:2][NH2:3].[CH3:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1.Cl>[OH-].[Na+].CCOCC>[CH3:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:1][C:2]#[N:3])=[O:10])=[CH:7][CH:6]=1To a solution of cyanamide (1.05 g, 0.025 mmol) in 25 ml of sodium hydroxide (10%) was added slowly to a solution of 4-methylbenzoyl chloride (3.3 ml, 0.025 mmol) in ether (8 ml). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture then was cooled in ice bath and acidified with hydrochloric acid (10%) to pH 2. The white solid separated was filtered, washed with water, later hexanes and dried under high vacuum to give the N-(4-methylbenzoyl)cyanamide (3.4 g); m.p. 140–142° C. (lit m.p. 149–150° C.); purity 88% HPLC; 1H-NMR (CD3OD) δ 2.42 (s, 3H, CH3), 7.38 (d, 2H, ArH), 7.78 (d, 2H, ArH).
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