Benzene, 1-isocyanato-2-methoxy- → N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-phenyl}-N'-(2-methoxyphenyl)urea

HRID 1857220Notes

Reaction equation

HRID 1857220 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]=[C:32]=[O:33].CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:32]([NH:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[O:24][CH3:23])=[O:33])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 21226206Ethyl acetate hexane

Product 1

HCID 22667241N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-phenyl}-N'-(2-methoxyphenyl)ureaYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinazoline (100 mg) was dissolved in toluene (10 ml) with heat, 2-methoxyphenyl isocyanate (0.36 ml) was added, and the admixture was refluxed with heat for 40 minutes. After removing the solvent by distillation, the resulting residue was purified by column chromatography on silica gel eluting with chloroform/methanol (100/1) and then with chloroform/acetone (5/1) to obtain 112 mg of the title compound (yield: 75%).

Workup

  1. temperaturewith heat
  2. temperaturethe admixture was refluxed
  3. temperaturewith heat for 40 minutes
  4. customAfter removing the solvent
  5. distillationby distillation
  6. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/methanol (100/1)

Sources & evidence

ORD record
ord-7e3cbc28676f4d1da82fe77424703d4f
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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