Triphosgene → HCID 22667128, compound

HRID 1008349Notes

Reaction equation

HRID 1008349 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])=[C:18]([F:23])[CH:17]=1.ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.[CH2:36]([NH2:39])[C:37]#[CH:38].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C.ClCCl>[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:28]([NH:39][CH2:36][C:37]#[CH:38])=[O:34])=[C:18]([F:23])[CH:17]=1

Participants

8

Reactant 4

HCID 94429TriphosgeneHCID 239041PropargylamineHCID 516892Sodium BicarbonateHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 1

HCID 22667128HCID 22667128, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (150 mg) was dissolved in chloroform (10 ml) and triethylamine (2 ml), and a solution of triphosgene (156 mg) in dichloromethane was added to the solution. The mixture was heated under reflux for 10 min. Next, propargylamine (53 mg) was added, and the mixture was heated under reflux for additional 30 min. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/acetone (2/1) to give 164 mg (yield 87%) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 10 min
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for additional 30 min
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customThe residue was purified by chromatography on silica gel by development with chloroform/acetone (2/1)

Sources & evidence

ORD record
ord-be95a3cf04604df1973c528ea3eaf502
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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