(2,4-Dichlorophenoxy)Acetic Acid → HCID 21890576, compound

HRID 721632Notes

Reaction equation

HRID 721632 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH3:37][O:38][C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][C:48]=1[O:49][CH3:50])[N:45]=[CH:44][CH:43]=[C:42]2[O:51][C:52]1[CH:58]=[CH:57][C:55]([NH2:56])=[CH:54][CH:53]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:37][O:38][C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][C:48]=1[O:49][CH3:50])[N:45]=[CH:44][CH:43]=[C:42]2[O:51][C:52]1[CH:53]=[CH:54][C:55]([NH:56][C:6](=[O:8])[CH2:5][O:4][C:3]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:2]=2[Cl:1])=[CH:57][CH:58]=1

Participants

7

Reactant 5

HCID 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 21890576HCID 21890576, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(2,4-Dichlorophenoxy)acetic acid (310 mg) was added to chloroform (5 ml), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (403 mg), 1-hydroxybenzotriazole monohydrate (284 mg), and 4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (498 mg) were added thereto. The mixture was then stirred with heating under reflux for 2 hr. A saturated aqueous sodium hydrogencarbonate solution was added to stop the reaction, and the reaction solution was extracted with chloroform, followed by washing with a saturated aqueous sodium hydrogencarbonate solution, 1 N hydrochloric acid, water, and saturated brine. The extract was then dried over sodium sulfate. After the concentration of the extract, the residue was purified on a column using chloroform/methanol to give N1-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-2-(2,4-dichlorophenoxy)acetamide (500 mg, yield 72%).

Workup

  1. additionwere added
  2. temperaturewith heating
  3. temperatureunder reflux for 2 hr
  4. customthe reaction
  5. extractionthe reaction solution was extracted with chloroform
  6. washby washing with a saturated aqueous sodium hydrogencarbonate solution, 1 N hydrochloric acid, water, and saturated brine
  7. dry with materialThe extract was then dried over sodium sulfate
  8. customAfter the concentration of the extract, the residue was purified on a column

Sources & evidence

ORD record
ord-431064718af842619408ab84171e4b73
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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