Dimethyl Sulfoxide → 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-methoxyaniline

HRID 720965Notes

Reaction equation

HRID 720965 reaction equation
[H-].[Na+].CS(C)=O.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[O:15][CH3:16].Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][N:19]=1>O>[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:30][CH3:31])[N:21]=[CH:20][N:19]=[C:18]2[O:14][C:11]1[CH:12]=[CH:13][C:8]([NH2:7])=[C:9]([O:15][CH3:16])[CH:10]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 198180564-Amino-3-methoxyphenol

Product 1

HCID 218899914-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-methoxyanilineYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride (60 wt %, 3.2 g) was added to dimethyl sulfoxide (50 ml), and the mixture was stirred at 50° C. for 20 min. 4-Amino-3-methoxyphenol (5.6 g) was added thereto, and the mixture was stirred at room temperature for 10 min. Next, 4-chloro-6,7-dimethoxyquinazoline (7.0 g) was added thereto, and the mixture was stirred at 100° C. overnight. Water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. Methanol was added to the residue, and the precipitated crystal was collected by suction filtration to give the title compound (7.3 g, yield 72%).

Workup

  1. stirringthe mixture was stirred at room temperature for 10 min
  2. stirringthe mixture was stirred at 100° C. overnight
  3. extractionthe mixture was extracted with chloroform
  4. washThe chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. additionMethanol was added to the residue
  8. filtrationthe precipitated crystal was collected by suction filtration

Sources & evidence

ORD record
ord-956effa2774b4046b38c6256d81a26bc
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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