Hydrochloric Acid → HCID 89656451, Verbindung

HRID 633547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633547
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

A solution of the product from Example 51B (2.8 g, 9.32 mmol) in dioxane (20.0 mL) at 0° C. was treated with concentrated hydrogen chloride (40 mL, 9.32 mmol), stirred for 15 minutes and treated with a solution of sodium nitrite (0.772 g, 11.19 mmol) in water (10 mL). The mixture was stirred for 1 hour at 0° C., treated with a solution of potassium iodide (3.10 g, 18.65 mmol) in water (10 mL) and stirred for 1 hour at ambient temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium thiosulfate, water, saturated aqueous sodium chloride, dried (MgSO4), filtered, and concentrated. Purification by chromatography (silica gel, 0-60% ethyl acetate in hexane) afforded the title compound (2.24 g, 58%).

Aufarbeitung

  1. stirringThe mixture was stirred for 1 hour at 0° C.
  2. stirringstirred for 1 hour at ambient temperature
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated sodium thiosulfate, water, saturated aqueous sodium chloride
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica gel, 0-60% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-58f4df414ecd477aa5253566397afafa
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321764B2

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