反应详情

1,2,5,6-Tetrahydro-3-methyl-1-oxobenzo[f]quinazolin-9-sulfonyl chloride (0.53 g, 1.7 mmole) and p-nitroaniline (0.25 g, 1.8 mmole) (Eastman) were dissolved in pyridine (5 ml) and the reaction mixture stirred at room temperature for 48 hours. The pyridine was removed in vacuo, and the residue washed with water. The dried solid was subjected to chromatography on silica (80 g), eluting with methanolmethylene chloride (1:19). Fractions containing product were evaporated to dryness, the residue sonicated with ether (75 ml) and filtered. The beige solid was washed with ether and dried under high vacuum to yield 1,2,5,6-tetrahydro-3-methyl-4′-nitro-1-oxobenzo[f]quinazoline-9-sulfonanilide. (0.18 g, 26%). Mp>240° C. 1H NMR (DMSO-d6, 300 MHz) δ: 2.32 (s, 3H, CH3); 2.72 (m, 2H, ArCH); 2.91 (m, 2H, ArCH2); 7.33 (d, J=9 Hz, 2H, Ar); 7.43 (d, J=8 Hz, 1H, Ar); 7.69 (dd, J=2,8 Hz, Ar); 8.13 (d, J=9 Hz, 2H, Ar); 9.23 (d, J=2 Hz, 1H, Ar); 11.13 (s, 1H, NH); 12.73 (s, 1H, NH). Anal Calculated for C19H16N4O5S.13/25H2O: C, 54.10; H, 4.07; N, 13.28; S, 7.60. Found: C, 54.07; H, 3.98; N, 13.19; S, 7.66.

1. customThe pyridine was removed in vacuo
2. washthe residue washed with water
3. washeluting with methanolmethylene chloride (1:19)
4. additionFractions containing product
5. customwere evaporated to dryness
6. customthe residue sonicated with ether (75 ml)
7. filtrationfiltered
8. washThe beige solid was washed with ether
9. customdried under high vacuum