4-Methylbenzyl alcohol → HCID 21890199, compound

HRID 720966Notes

Reaction equation

HRID 720966 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:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.[C:23]1([CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.Cl[C:38](Cl)([O:40][C:41](=[O:47])OC(Cl)(Cl)Cl)Cl.CC1C=CC(CO)=CC=1>C(Cl)Cl>[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:22]=[CH:21][C:19]([NH:20][C:41](=[O:47])[O:40][CH2:38][C:26]2[CH:27]=[CH:28][C:23]([CH3:29])=[CH:24][CH:25]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 115054-Methylbenzyl alcoholHCID 94429TriphosgeneHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 22504574Toluene triethylamine

Product 1

HCID 21890199HCID 21890199, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (129 mg) was added to toluene/triethylamine=10/1 (10 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (193 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 4-methylbenzyl alcohol (79 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed to cool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated, and the residue was purified on a column using chloroform/methanol to give the title compound (108 mg, yield 51%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customto prepare a solution
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 15 min
  6. temperaturewith heating
  7. temperatureunder reflux for 2 hr
  8. customAfter the completion of the reaction
  9. distillationbefore distilled water
  10. additionwas added
  11. extractionThe mixture was subjected to separatory extraction with chloroform
  12. washby washing with a 1 N aqueous hydrochloric acid solution and saturated brine
  13. dry with materialThe washed solution was dried over sodium sulfate
  14. concentrationwas concentrated
  15. customthe residue was purified on a column

Sources & evidence

ORD record
ord-9c78a7a84354457eab9145a1aac06472
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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