Chlorophenyl Quinazolin-4-Marin Analysis

6,8-dibromo-2-(4-chlorophenyl)quinazolin-4-amine (IV)
A mixture of chloro compound III ( 0.01 mol) and ammonium acetate (2.3 g, 0.3 mol) in pyridine was refluxed for 20 h. The reaction mixture was cooled and then poured onto crushed ice. The obtained solid was filtered off and recrystallized from ethanol. m.p. 270oC , 75% yield. Analysis calculated for C14H8Br2ClN3; Calcd.: %C, C, 40.67; H, 1.95; N, 10.16, Found: % C 40.70; H, 1.99; N,10.10. IR: υmax./cm-1 3250, 3140 (NH2), 3010 (C-H aromatic), 1620 (C=N) and at 1600 (C=C). 1H-NMR (DMSO-d6, ppm): δ 7.5-8.5 (m, 6H, Ar-H ) and at 12.9( 2H, s, NH2, exchangeable with D2O). 13C NMR (DMSO-d6):163, 161, 149, 140, 133, 135, 129.4, 129, 125, 122, 120, 114. MS: m/z = 417

6,8-dibromo-2-(4-chlorophenyl)-4-hydrazinylquinazoline (V)
Chloro compound III ( 0.01 mol) and hydrazine hydrate 99% (0.05 mol) (1:5) was
110oC , 80% yield. Analysis calculated for C21H13Br2ClN4; Calcd.: %C, C, 48.82; H, 2.54; N, 10.84, Found: % C 48.90; H, 2.59; N,10.90. IR: υmax./cm-1 3250 (NH), 3000 (C-H aromatic), 1630 (C=N) and at 1600 (C=C). 1H-NMR (DMSO-d6, ppm): δ 7.4-8.4 (m, 11H, Ar-H ), 8.7 ( 1H, s, CH=N) and at 12.0 ( 1H, s, NH, exchangeable with D2O). 13C NMR (DMSO-d6):170, 165, 150, 144, 142, 135, 133.5, 132.4, 131, 130, 129.5, 128.9, 128.7, 126, 121, 120, 116. MS: m/z = 520

6,8-dibromo-4-(2-(4-chlorobenzylidene)hydrazinyl)-2-(4-chlorophenyl)quinazoline (VIb)
Crystalized from ethanol m.p. 130oC , 80% yield. Analysis calculated for C21H12Br2Cl2N4; Calcd.: %C, C, 45.77; H, 2.19; N, 10.17, Found: % C 45.90; H, 2.22; N,10.20. IR: υmax./cm-1 3300 (NH), 3100 (C-H aromatic), 1650 (C=N) and at 1620 (C=C). 1H-NMR (DMSO-d6, ppm): δ 7.5-8.5 (m, 10H, Ar-H ), 8.9 ( 1H, s, CH=N) and at 12.2 ( 1H, s, NH, exchangeable with D2O). 13C NMR (DMSO-d6):175, 165, 152, 145, 142, 137, 135, 133, 130, 129, 128.5, 127, 122, 120, 117. MS: m/z =