Dabco → 3-chloro-4-fluoro-N-pyrimidin-4-ylbenzenesulfonamide

HRID 46340

Reaktionsgleichung

Reaktionsgleichung von HRID 46340
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.C1N2CCN(CC2)C1.[Cl:16][C:17]1[CH:18]=[C:19]([S:24](Cl)(=[O:26])=[O:25])[CH:20]=[CH:21][C:22]=1[F:23]>C(#N)C>[Cl:16][C:17]1[CH:18]=[C:19]([S:24]([NH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][N:3]=2)(=[O:25])=[O:26])[CH:20]=[CH:21][C:22]=1[F:23]

Komponenten

5

Edukt 3

HCID 9237DabcoHCID 689584-AminopyrimidineHCID 1452223-Chloro-4-fluorobenzenesulphonyl chloride

Produkt 1

HCID 594364913-chloro-4-fluoro-N-pyrimidin-4-ylbenzenesulfonamideAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-Aminopyrimidine (1.0 g, 10.5 mmol) and DABCO™ (1.18 g, 10.5 mmol) were added concurrently to a solution of 3-chloro-4-fluorobenzenesulfonyl chloride (1.25 mL, 10.0 mmol) in anhydrous acetonitrile (49 mL). The reaction mixture immediately turned yellow and a precipitate was formed. After stirring for 16 hours, the mixture was concentrated in vacuo. The crude material was suspended in ethyl acetate (75 mL) and water (75 mL) and stirred for 15 minutes. The resulting solid was filtered and dried in vacuo to afford the title compound, 0.83 g, 27% yield.

Aufarbeitung

  1. customThe reaction mixture immediately turned yellow and a precipitate was formed
  2. concentrationthe mixture was concentrated in vacuo
  3. stirringwater (75 mL) and stirred for 15 minutes
  4. filtrationThe resulting solid was filtered
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-257ca3bd31f446f79a741ae7a987f53f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

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