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Triphosgene → HCID 21891049, compound

HRID 720980
Notes
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Reaction equation

HRID 720980 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.ClC(Cl)(O[C:43](=[O:49])[O:44][C:45](Cl)(Cl)Cl)Cl.[Cl:51][C:52]1[CH:62]=[CH:61][CH:60]=[CH:59][C:53]=1[O:54][CH2:55][CH2:56]CO>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:43](=[O:49])[O:44][CH2:45][CH2:56][CH2:55][O:54][C:53]2[CH:59]=[CH:60][CH:61]=[CH:62][C:52]=2[Cl:51])=[C:18]([CH3:23])[C:17]=1[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 94429TriphosgeneHCID 122931873-(2-Chlorophenoxy)propan-1-olHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylanilineHCID 22504574Toluene triethylamine

Product 1

HCID 21891049HCID 21891049, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (78 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 (117 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 3-(2-chlorophenoxy)-1-propanol (67 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 (80 mg, yield 58%).

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-a3e43d0dc78a4ceda929288d17f7b808
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07135466B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes