Water → HCID 71144039, Verbindung

HRID 509315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 509315
[CH3:1][C:2]([S@@:5](/[N:7]=[CH:8]/[C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:6])([CH3:4])[CH3:3].[Cl:19][C:20]1[CH:21]=[C:22]([Mg]Br)[CH:23]=[CH:24][C:25]=1[Cl:26].[NH4+].[Cl-].O>C1COCC1.CCOC(C)=O>[Cl:19][C:20]1[CH:21]=[C:22]([C@@H:8]([C:9]2[C:14]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:12]=[CH:11][N:10]=2)[NH:7][S@:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[CH:23]=[CH:24][C:25]=1[Cl:26]

Komponenten

7

Edukt 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 89310312HCID 89310312, VerbindungHCID 178478192HCID 178478192, Verbindung

Produkt 1

HCID 71144039HCID 71144039, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(S,E)-2-Methyl-N-((3-(trifluoromethyl)pyridin-2-yl)methylene)propane-2-sulfinamide (0.493 g, 1.772 mmol) was dissolved in dry THF (10 mL) and cooled in an ice bath. 3,4-Dichlorophenylmagnesium bromide (Aldrich, 0.5 M solution in THF, 4.0 mL, 2.0 mmol) was added, and the reaction was stirred for 5 minutes. Saturated aqueous NH4Cl (10 mL), H2O (100 mL) and EtOAc (100 mL) were added and the phases were mixed and separated. The organic layer was dried with MgSO4 and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to EtOAc gradient) gave (S)—N—((S)-(3,4-dichloro-phenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. additionthe phases were mixed
  3. customseparated
  4. dry with materialThe organic layer was dried with MgSO4
  5. customevaporated to dryness under reduced pressure
  6. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-4528fbbc36dc474a82bd46b6deb4d029
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096527B2

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