Water → 4-(4-Iodophenoxy)-6,7-dimethoxyquinazoline

HRID 2213855Notes

Reaction equation

HRID 2213855 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[I:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1.O>CN(C)C=O>[I:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 219588884-(4-Iodophenoxy)-6,7-dimethoxyquinazolineYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-6,7-dimethoxyquinazoline (224 mg, 1.00 mmol), potassium carbonate (152 mg, 1.10 mmol) and 4-iodophenol (244 mg, 1.10 mmol) in dimethylformamide (4 ml) was heated at 110° C. for 2 hours before the reaction was allowed to cool to ambient temperature. The reaction was poured into water and the solid which had precipitated was collected by suction filtration and washed with a mixture of diethyl ether (10 ml), ethyl acetate (10 ml) and isohexane (10 ml). Drying of this material yielded, yielded 4-(4-iodophenoxy)-6,7-dimethoxyquinazoline (340 mg, 83% yield) as a white solid:

Workup

  1. customthe solid which had precipitated
  2. filtrationwas collected by suction filtration
  3. washwashed with a mixture of diethyl ether (10 ml), ethyl acetate (10 ml) and isohexane (10 ml)
  4. customDrying of this material
  5. customyielded

Sources & evidence

ORD record
ord-4c55278a13b04e2a8e2ae9b1a2a63e6b
Source dataset
uspto-grants-2006_09
Patent number
US07105669B1

Reaction notes

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