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Dimethylformamide → 4-{[2-(2,4-Dichlorophenoxy)-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine

HRID 38797
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 38797
Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])=[CH:4][N:3]=1.[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[OH:28].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>C(OCC)(=O)C>[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[O:28][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])=[CH:4][N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 84492,4-DichlorophenolHCID 10796Cesium carbonateHCID 581687074-{[2-Chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine

Produkt 1

HCID 581689174-{[2-(2,4-Dichlorophenoxy)-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholineAusbeute 14,8 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-{[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine (170 mg), 2,4-dichlorophenol (112 mg), cesium carbonate (225 mg), and N,N-dimethyl formamide (2 mL) was stirred at room temperature for 15 hours, and then at 100° C. for 10 hours. To the reaction liquid was added ethyl acetate (30 mL), followed by washing with saturated brine (20 mL) and a saturated aqueous ammonium chloride solution (20 mL) in this order, the organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform-ethyl acetate) to obtain 4-{[2-(2,4-dichlorophenoxy)-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine (36 mg) as a brown oily substance.

Aufarbeitung

  1. waitat 100° C. for 10 hours
  2. customTo the reaction liquid
  3. washby washing with saturated brine (20 mL)
  4. dry with materiala saturated aqueous ammonium chloride solution (20 mL) in this order, the organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ede3ef95ab5b46a7921b21cd3ced2f4f
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08524727B2

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