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Triphosgene → HCID 21889867, compound

HRID 721378
Notes
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Reaction equation

HRID 721378 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[C:22]([CH3:23])=[CH:21][C:19]([NH2:20])=[C:18]([CH3:24])[CH:17]=1.Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl.[O:37]1[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][CH:45]([OH:49])[CH2:46][CH2:47][CH3:48])[CH2:39][CH2:38]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C.C1(C)C=CC=CC=1>[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[C:22]([CH3:23])=[CH:21][C:19]([NH:20][C:26](=[O:28])[O:49][CH:45]([CH2:44][CH2:43][N:40]2[CH2:41][CH2:42][O:37][CH2:38][CH2:39]2)[CH2:46][CH2:47][CH3:48])=[C:18]([CH3:24])[CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 218904214-((6,7-Dimethoxyquinolin-4-yl)oxy)-2,5-dimethylanilineHCID 21890612HCID 21890612, compound

Product 1

HCID 21889867HCID 21889867, compoundYield 89.3%

Reagents, catalysts & solvents 3

HCID 1140
Toluene
Solvent
HCID 6344DichloromethaneSolvent
HCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline (50 mg) was added to toluene (5 ml), and triethylamine (0.5 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (68 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 1-morpholino-3-hexanol (43 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, and the extract was washed with water and saturated brine in that order. The extract was dried over sodium sulfate and was then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (74 mg, yield 81%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customto prepare a solution
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 10 min
  6. temperaturewith heating
  7. temperatureunder reflux for 3 hr
  8. customthe reaction
  9. extractionthe reaction solution was then extracted with chloroform
  10. washthe extract was washed with water and saturated brine in that order
  11. dry with materialThe extract was dried over sodium sulfate
  12. concentrationwas then concentrated
  13. customThe residue was purified on a column

Sources & evidence

ORD record
ord-88babc19a3e5421cb43b93ad0ec66652
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