1,1-Dichloroethane → (6-Iodoquinazolin-4-yl)-(3-methyl-4-phenoxy-phenyl)-amine

HRID 1264051Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH2:17].ClC(Cl)C>C(O)(C)(C)C>[I:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][N:3]=[C:2]2[NH:17][C:16]1[CH:18]=[CH:19][C:20]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([CH3:13])[CH:15]=1

Participants

Conditions

Temperature: 90 °C

Procedure

The 4-chloro-6-iodo-quinazoline (5.0 g, 17.2 mmol) and the 3-methyl-4-phenoxyaniline (17.2 mmol) were mixed together in 1:1 dichloroethane and t-butanol (50 ml). The reaction mixture was heated at 90° C. for 4 hours whereupon a yellow precipitate was observed. The reaction was cooled down and the precipitate was collected and afforded (6-iodo-quinazolin-4-yl)-(3-methyl-4-phenoxy-phenyl)-amine. (8.0 g, 94%). M/z, 454. 1H NMR (CD3OD): δ: 9.12(s, 1H), 8.83(s, 1H), 8.39 (d, 1H, J=8.8 Hz), 7.63(d, 1H, J=8.8 Hz), 7.55 (d, 1H, J=2.1 Hz), 7.35(dd,1H, J1=J2=8.5 Hz), 7.28(t, 2H, J=8.1 Hz, ), 7.05 (t, J=8.5 Hz), 6.87(d, 1H, J=8.1 Hz), 3.81 (s, 3H).

Workup

temperatureThe reaction was cooled down
customthe precipitate was collected

Sources & evidence

ORD record: ord-f1214ae0559e4d23b162c482b4aefd50
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541481B2

Reaction notes

Loading…