Triethylamine → 1-(N-Formyl-N-phenylamino)methyl-5-chloropyrimidin-2-one

Participants

Reaction Conditions

Reaction Steps

5-Chloropyrimidin-2-one hydrochloride (3.0 mmol) and triethylamine (6 mmol) were stirred together in CH2Cl2 (50 ml) for 15 minutes before a solution of N-chloromethylformanilide (see Prepartion 12) (3 mmol) in CH2Cl2 was added. The mixture was stirred at 40° C. for 18 hours before the solvent was distilled off. The residue was washed with water and ether. Yield: 0.79 g (50%), m. p. 200° C. (EtOH). 1H NMR (DMSO-d6, δ): 5.68 (s, CH2), 7.32 (Ph), 8.05-8.65 (CHO, H-4 and H-6). IR (KBr, cm-1): 1660 (CO), 1680 (CO). MS (70 eV, m/e (% rel. int.)): 263 (M+, 1), 143 (7), 134 (41), 116 (6), 107 (6), 106 (100), 105 (57), 104 (10), 79 (10), 78 (7), 77 (41), 52 (11), 51 (20).

Provenance & Evidence