Thionyl Chloride → methyl 3-(8-cyano-6-iodo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate

Participants

Reaction Steps

To a stirred solution of methyl 3-[8-(aminocarbonyl)-6-iodo-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate in DMF (15 ml) was added thionyl chloride (1.79 ml). The reaction mixture was stirred at room temperature for 30 minutes and ice-water added. The resultant mixture was extracted with methylene chloride (×2) and the combined organic layers washed with water, saturated NaHCO3 solution, dried (magnesium sulphate) and concentrated to yield methyl 3-(8-cyano-6-iodo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate as a white solid (2.04 g); NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 3.88 (s, 3H), 7.61 (d, 1H), 8.03 (m, 2H), 8.53 (s, 1H), 8.67 (d, 1H), 8.74 (d, 1H); Mass Spectrum: M+H+ 446.

Provenance & Evidence