Dimethyl Sulfoxide → HCID 11516373, Verbindung

HRID 1987224

Reaktionsgleichung

Reaktionsgleichung von HRID 1987224
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[F:17][C:18]1([F:26])[CH2:23][CH2:22][CH:21]([CH2:24][NH2:25])[CH2:20][CH2:19]1.CS(C)=O.C(CN)O>O>[F:17][C:18]1([F:26])[CH2:23][CH2:22][CH:21]([CH2:24][NH:25][C:2]2[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:4][C:3]=2[N+:14]([O-:16])=[O:15])[CH2:20][CH2:19]1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 700EthanolamineHCID 3286362N-(4-fluoro-3-nitrophenyl)ethanesulfonamide2×HCID 156044941-(4,4-Difluorocyclohexyl)methanamine

Produkt 1

HCID 11516373HCID 11516373, VerbindungAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

N-(4-Fluoro-3-nitrophenyl)ethanesulfonamide (26 g, 0.107 mol), [(4,4-difluorocyclohexyl)methyl]amine (approx. 15 g), DIPFA (20 mL) and DMSO (100 mL) were mixed together and heated to 65° C. overnight. Ethanolamine (5 g) was added and the reaction mixture was stirred until complete disappearance of N-(4-fluoro-3-nitrophenyl)ethanesulfonamide (approx. 4-5 hrs.). The room temperature cooled down reaction mixture was poured in cold water (900 mL). The product was extracted with DCM (5×200 mL). The combined organic phases were washed with HCl 2N (3×200 mL) and dried over anhydrous Na2SO4. The solvent was removed and the crude product was purified on silica gel by flash chromatography (this material can be re-crystallized using a mixture of EtOAc and hexane) to provide the title product (24.2 g) as orange solid.

Aufarbeitung

  1. temperatureThe room temperature cooled down
  2. customreaction mixture
  3. extractionThe product was extracted with DCM (5×200 mL)
  4. washThe combined organic phases were washed with HCl 2N (3×200 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed
  7. customthe crude product was purified on silica gel by flash chromatography (this material
  8. customcan be re-crystallized
  9. additiona mixture of EtOAc and hexane)

Quellen und Nachweise

ORD-Eintrag
ord-98c8825b80c04d309453a53714842663
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550495B2

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