Water → HCID 71144039, Verbindung

HRID 1622555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1622555
[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 89310312(NE,S)-2-methyl-N-[[3-(trifluoromethyl)pyridin-2-yl]methylidene]propane-2-sulfinamideHCID 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 mixture 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 magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to EtOAc gradient) gave (S)—N—((S)-(3,4-dichlorophenyl)(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 magnesium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-b38f987e44b142409653ca0d12cbd05d
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778941B2

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