Ammonia → 2-acetamido-N-(4-nitrophenyl)benzamide

Participants

Reaction Conditions

Reaction Steps

4-Amino-N-(4-nitrophenyl)benzamide (C1) (730 mg, 2.84 mmol) and 4-chloro-6-methyl-2-pyrimidinylamine (A8) (416 mg, 2.84 mmol) were dissolved in warm 2-ethoxyethanol (20 mL), two drops c.HCl was then added to the reaction mixture was refluxed for 40 min. by which time TLC and MS showed the completion of the reaction. The reaction mixture was diluted with ethyl acetate and cooled to 20° C. The resulting precipitate was filtered and washed with more EtOAc to give a solid product. This was suspended in MeOH and basified with aqueous NH3 and diluted with water. The resulting precipitate was filtered and dried to give C2 (671 mg). The filtrate was concentrated to give a further 276 mg of C2 (92% overall): mp (MeOH)>300° C.; 1H NMR [(CD3)2SO] δ 10.59 (s, 1H, NH), 9.37 (s, 1H, NH), 8.27-8.24 (m, 2H, ArH), 8.09-8.06 (m, 2H, ArH), 8.05-7.90 (m, 4H, ArH), 6.25 (s, 2H, NH2), 5.96 (s, 1H, ArH), 2.16 (s, 3 H, CH3); Mass APCl+365.

Provenance & Evidence