Chlorobenzene → HCID 21890463, compound

HRID 721626Notes

Reaction equation

HRID 721626 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1NC(=O)OCC1C=CC(OC)=C(OC)C=1.ClC1[C:48]2[C:43](=[CH:44][C:45]([O:51][CH3:52])=[C:46]([O:49][CH3:50])[CH:47]=2)N=CN=1.[C:53](=[O:56])([O-])O.[Na+].Cl[C:59]1C=CC=CC=1>>[CH3:20][O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:21][CH3:22])[N:12]=[CH:11][N:10]=[C:9]2[O:8][C:6]1[CH:7]=[CH:2][C:3]([O:56][CH2:53][CH2:59][CH2:52][O:51][C:45]2[CH:44]=[CH:43][CH:48]=[CH:47][C:46]=2[O:49][CH3:50])=[CH:4][CH:5]=1

Participants

5

Reactant 4

HCID 7964ChlorobenzeneHCID 516892Sodium BicarbonateHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 21891141HCID 21891141, compound

Product 1

HCID 21890463HCID 21890463, compoundYield 37%

Conditions

Temperature
140 °C

Procedure

Chlorobenzene (0.4 ml) was added to the compound (3) (205 mg) and 4-chloro-6,7-dimethoxyquinazoline (252 mg), and the mixture was stirred at 140° C. overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform, followed by washing with saturated brine. The extract was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel using hexane/acetone for development to give the title compound (128 mg, yield 37%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washby washing with saturated brine
  3. dry with materialThe extract was then dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d8aedf0d34164b14804573592a6867cc
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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