Pyridine → HCID 86707263, Verbindung

HRID 576045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576045
N1C=CC=CC=1.CN(C1C=CC=CN=1)C.[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.[F:24][C:25]([F:42])([F:41])[C:26]([N:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([S:37](Cl)(=[O:39])=[O:38])[CH:34]=2)[CH2:29]1)=[O:27]>C(Cl)(Cl)Cl>[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][S:37]([C:33]2[CH:34]=[C:35]3[C:30](=[CH:31][CH:32]=2)[CH2:29][N:28]([C:26](=[O:27])[C:25]([F:42])([F:24])[F:41])[CH2:36]3)(=[O:38])=[O:39])=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 97314-FluoroanilineHCID 218852-DimethylaminopyridineHCID 867072642,3-Dihydro-2-(2,2,2-trifluoroacetyl)-1H-isoindole-5-sulfonyl chloride

Produkt 1

HCID 86707263HCID 86707263, VerbindungAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Pyridine (2.57 mL, 31.9 mmol) and dimethylaminopyridine (195 mg, 1.59 mmol) were added to a solution of 4-fluoroaniline (1.86 g, 16.7 mmol) in chloroform (46 mL) at room temperature and the mixture was cooled in ice. 2-(Trifluoroacetyl)-2,3-dihydro-1 H-isoindole-5-sulfonyl chloride (5.00 g, 15.9 mmol) was added thereto and the mixture was warmed to room temperature and stirred for 15 hr. The reaction mixture was concentrated under reduced pressure and the residue was diluted with ethyl acetate. The mixture was washed with 1 mol/L hydrochloric acid and brine, the organic layer was dried over anhydrous magnesium sulfate, and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was powdered with diethyl ether and collected by filtration to afford the title compound as a pale pink powder (5.85 g).

Aufarbeitung

  1. temperaturethe mixture was cooled in ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washThe mixture was washed with 1 mol/L hydrochloric acid and brine
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationthe desiccant was filtered off
  7. concentrationfollowed by concentration under reduced pressure
  8. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-1a3473361da749be83dd5099d4e2951b
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09035059B2

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