Hydrochloric Acid → HCID 89656451, Verbindung

HRID 930891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 930891
N[C:2]1[CH:3]=[C:4]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16].Cl.N([O-])=O.[Na+].[I-:26].[K+]>O1CCOCC1.O>[F:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][C:7]1[CH:6]=[CH:5][C:4]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:3][C:2]=1[I:26]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 89656036HCID 89656036, Verbindung

Produkt 1

HCID 89656451HCID 89656451, VerbindungAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of Example 146b (2.8 g, 9.32 mmol) in dioxane (20 mL) at 0° C. was added concentrated hydrochloric acid (40 mL, 9.32 mmol). The mixture was stirred 15 minutes and a solution of sodium nitrite (0.772 g, 11.19 mmol) in water (10 mL) was added. The mixture was stirred for 1 hour at 0° C. A solution of potassium iodide (3.10 g, 18.7 mmol) in water (10 mL) was added and stirring was continued 1 hour at ambient temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium thiosulfate, water, and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-60% ethyl acetate in hexane) to provide the title compound (2.24 g, 58.4% yield).

Aufarbeitung

  1. stirringThe mixture was stirred for 1 hour at 0° C
  2. stirringstirring
  3. waitwas continued 1 hour at ambient temperature
  4. customThe mixture was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated sodium thiosulfate, water, and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography (silica gel, 0-60% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fabc4f815a3347ae86df4fa262dd4eae
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296741B2

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