Triphosgene → HCID 21890331, compound

HRID 721131Notes

Reaction equation

HRID 721131 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]([CH3:23])[C:17]=1[CH3:24].C1(C)C=CC=CC=1.C(N(CC)CC)C.Cl[C:40](Cl)([O:42]C(=O)OC(Cl)(Cl)Cl)Cl.[C:51]1([CH:57]([OH:61])[CH2:58][CH2:59][CH3:60])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=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][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:40](=[O:42])[O:61][CH:57]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:58][CH2:59][CH3:60])=[C:18]([CH3:23])[C:17]=1[CH3:24]

Participants

6

Reactant 4

HCID 94429TriphosgeneHCID 953721-Phenyl-1-butanolHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylanilineHCID 22504574Toluene triethylamine

Product 1

HCID 21890331HCID 21890331, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (90 mg) was added to toluene/triethylamine=10/1 (9 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (125 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux form 15 min. Subsequently, 1-phenyl-1-butanol (62 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. The residue was purified on a column using chloroform/methanol to give the title compound (59 mg, yield 40%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customto prepare a solution
  4. temperaturethe mixture was heated
  5. temperatureunder reflux
  6. customform 15 min
  7. temperaturewith heating
  8. temperatureunder reflux for 2 hr
  9. customAfter the completion of the reaction
  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-9192a5379caa4351a3e996793f52e256
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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