Sulfuryl chloride → HCID 57800294, Verbindung

HRID 913584

Reaktionsgleichung

Reaktionsgleichung von HRID 913584
S(Cl)([Cl:4])(=O)=O.[CH3:6][O:7][C:8]1[CH:20]=[CH:19][C:11]2[NH:12][C:13]([C:15]([F:18])([F:17])[F:16])=[N:14][C:10]=2[CH:9]=1.C([O-])(O)=O.[Na+]>CC(O)=O.CCOC(C)=O.O>[Cl:4][C:9]1[C:10]2[N:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[NH:12][C:11]=2[CH:19]=[CH:20][C:8]=1[O:7][CH3:6]

Komponenten

7

Edukt 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 178488085HCID 178488085, Verbindung

Produkt 1

HCID 57800294HCID 57800294, VerbindungAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sulfuryl chloride (0.39 mL, 4.86 mmol) was added dropwise to a 0° C. solution of 5-(methyloxy)-2-(trifluoromethyl)-1H-benzimidazole (1.0 g, 4.63 mmol) in HOAc (10 mL). The ice bath was removed and the mixture was allowed to stir at rt for 2 h. The concentrated reaction mixture was suspended in a mixture of EtOAc and H2O and the pH was adjusted to 7 with saturated aqueous NaHCO3. The reaction was partitioned and the aqueous portion was extracted with EtOAc. The combined organic fractions were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford the title compound (0.93 g): MS (ESI) m/z 251 (M+1).

Aufarbeitung

  1. customThe ice bath was removed
  2. customThe concentrated reaction mixture
  3. customThe reaction was partitioned
  4. extractionthe aqueous portion was extracted with EtOAc
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e89ff9bd5b1945dd89255e2146f0ff7e
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026262B2

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