Sodium Hydroxide → Chloroform methanol ammonia

Participants

Reaction Conditions

Reaction Steps

To 78 mg (0.7 mmol) of 4-Mercaptopyridine was added 34 mg (0.5 mmol) of solid NaOH in 1 ml of dry DNA. To the resulting solution, 134 mg (0.5 mmol) of quinazolinone (16) dissolved in 2 ml dry DMA was added. The mixture was kept under N2, and a finely ground catalyst mixture containing 44 mg CuBr and 22 mg Cu2O was added The mixture was stirred magnetically and heated to 135° C., until the reaction was complete as judged by TLC (anh. NH3 /MeOH/CHCl3 ; 0.5: 4.5: 9.5). The solvent was removed under high vacuum through a cryogenic trap cooled to -78° C. The desired product was isolated by flash chromatography (anh. NH3 /MeOH/CHCl3 ; 0.5: 4.5: 9.5) on silica, yielding 130 mg (89%) of (17) as a white powder. M.P. 248°-249° C. (dec.). IR (KBr) 3358, 3073, 2933, 1682, 1634, 1574, 1475, 1462, 1318, 1277, 1059, 835, 710 cm-1 ; 1H NMR (CDCl3) δ 2.36 (s, 3H), 3.84 (s, 3H), 6.90 (d, 2H, J=5.1 Hz), 7.48 (d, 1H, J=9.1 Hz), 7.79 (d, 1H, J=9.1 Hz), 8.28 (d, 2H, J=5.1 Hz), 10 86 (s, 1H). Anal. Calcd. For C15H13N3O2S: C, 60.18; H, 4.38; N, 14.04; S, 10.71. Found: C, 60.28; H, 4.43; N, 14.07; S, 10.63. HRMS Calcd. For C15H13N3O2S: 299.0730. Found: 299.0718.

Provenance & Evidence