Hydrochloric Acid → HCID 178488936, Verbindung

HRID 530731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530731
[CH:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:18]=[C:17]([O:19]CC3C=CC(OC)=CC=3)[C:16]3[C:11](=[C:12]([CH3:31])[CH:13]=[C:14]([O:29][CH3:30])[CH:15]=3)[N:10]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].[Cl-].[Cl-].[Cl-].[Cs+].[Cs+].[Cs+].[I-].[Na+].Cl>C(#N)C.O>[OH:19][C:17]1[C:16]2[C:11](=[C:12]([CH3:31])[CH:13]=[C:14]([O:29][CH3:30])[CH:15]=2)[N:10]=[C:9]([C:6]2[S:7][CH:8]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)[CH:18]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 20975861Cesium trichlorideHCID 666508822-(4-Isopropyl-thiazol-2-yl)-6-methoxy-4-(4-methoxy-benzyloxy)-8-methyl-quinoline

Produkt 1

HCID 178488936HCID 178488936, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Compound 222f (1.23 g, 2.82 mmol), cesium trichloride (1.58 g, 4.23 mmol), and sodium iodide (423 mg, 2.82 mmol) in ACN (26 mL) were stirred at 85° C. for 1 hr. The mixture was then filtered through celite and the solvent was evaporated. The brown solid obtained was suspended in water, pH was adjusted at 5 with 1N HCl. The mixture was extracted with DCM, dried over Na2SO4, filtered, concentrated under reduced pressure, and purified by chromatography on silica gel (petroleum ether/DCM) to yield compound 218f as a brown solid in 55% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.40 (d, J=6.91 Hz, 6H), 2.80 (s, 3H), 3.17-3.24 (m, 1H), 3.89 (s, 3H), 7.00 (s, 1H), 7.21 (m, 1H), 7.55 (s, 1H), 7.79 (s, 1H), 9.56 (brs, 1H).

Aufarbeitung

  1. filtrationThe mixture was then filtered through celite
  2. customthe solvent was evaporated
  3. customThe brown solid obtained
  4. extractionThe mixture was extracted with DCM
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified by chromatography on silica gel (petroleum ether/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-bc353e2f2e804e0b855143f24f75865e
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353100B2

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