Triphosgene → HCID 21890225, compound

HRID 721138Notes

Reaction equation

HRID 721138 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][CH: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(C)C=C[CH:26]=[CH:25][CH:24]=1.[CH2:30]([N:32]([CH2:35]C)CC)C.ClC(Cl)([O:40][C:41](=O)[O:42]C(Cl)(Cl)Cl)Cl>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][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:41](=[O:40])[O:42][CH2:23][CH2:24][CH2:25][CH2:26][N:32]([CH3:35])[CH3:30])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 94429TriphosgeneHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 22504574Toluene triethylamine

Product 1

HCID 21890225HCID 21890225, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (80 mg) was added to toluene/triethylamine=10/1 (8 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (130 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 4-dimethylaminopropanol (40 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 temperatures 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. The residue was purified on a column using chloroform/methanol to give the title compound (22 mg, yield 17%). Mass spectrometry value (ESI-MS, m/z): 441 (M++1)

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. temperatureto cool to room temperatures
  10. distillationbefore distilled water
  11. additionwas added
  12. extractionThe mixture was subjected to separatory extraction with chloroform
  13. washby washing with a 1 N aqueous hydrochloric acid solution and saturated brine
  14. dry with materialThe washed solution was dried over sodium sulfate
  15. concentrationwas concentrated
  16. customThe residue was purified on a column

Sources & evidence

ORD record
ord-f44157ad24bb4f70a87a0d2f177af291
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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