Potassium Carbonate → HCID 71256783, Verbindung

HRID 332678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 332678
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[O:9][CH2:8][CH2:7][O:6]1.[N:10]([CH:13]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:14]1[CH:15]=[C:16]([CH:28]=[CH:29][CH:30]=1)[O:17][CH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)=[N+:11]=[N-:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[N:10]([CH:13]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:14]1[CH:15]=[C:16]([CH:28]=[CH:29][CH:30]=1)[O:17][CH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([O:25][CH2:2][CH2:3][CH2:4][CH:5]2[O:9][CH2:8][CH2:7][O:6]2)=[O:24])=[CH:21][CH:20]=1)=[N+:11]=[N-:12]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 5520722-(3-Chloropropyl)-1,3-dioxolaneHCID 710930924-((3-(Azido(phenyl)methyl)phenoxy)methyl)benzoic acid

Produkt 1

HCID 71256783HCID 71256783, VerbindungAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 3-chloropropyl-1,3-dioxolane (0.2 g, 1.35 mmol) in dimethyl formamide (14 mL), was added 4-((3-(azido(phenyl)methyl)phenoxy)-methyl)benzoic acid (Example 51 Step 3) (0.5 g, 1.39 mmol) and potassium carbonate (0.38 g, 2.78 mmol). The reaction was allowed to stir at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (×3). The organic extracts were washed with brine, dried (sodium sulphate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford the title compound (0.63 g, 96%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (×3)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried (sodium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with 0-100% ethyl acetate in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-b9042890c5f44c6bb51eb443a27a6600
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877774B2

Notizen zur Reaktion

Wird geladen…