4-Toluenesulfonyl chloride → (S)-2-[p-(3-Chlorobutyloxy)phenyl]-5-n-hexylpyrimidine

HRID 274202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274202
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[Cl:12][C@@H:13]([CH3:17])[CH2:14][CH2:15][OH:16].[CH2:18]([C:24]1[CH:25]=[N:26][C:27]([C:30]2[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=2)=[N:28][CH:29]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:12][C@@H:13]([CH3:17])[CH2:14][CH2:15][O:16][C:33]1[CH:32]=[CH:31][C:30]([C:27]2[N:26]=[CH:25][C:24]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:29][N:28]=2)=[CH:35][CH:34]=1

Komponenten

6

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 641048(S)-3-chlorobutan-1-olHCID 30922104-(5-Hexyl-2-pyrimidinyl)phenol

Produkt 1

HCID 67801633(S)-2-[p-(3-Chlorobutyloxy)phenyl]-5-n-hexylpyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

26.3 g of (S)-3-chlorobutyl-1-tosylate, preparable from p-toluenesulfonyl chloride and (S)-3-chlorobutan-1-ol, and 27.2 g of 4-(5-n-hexylpyrimidin-2-yl)phenol are added to a suspension of 40 g of potassium carbonate in 200 ml of acetone. After 24 hours, boiling under reflux, the reaction mixture is filtered, the filtrate is freed from solvent and the residue is twice recrystallized from ethanol. (S)-2-[p-(3-Chlorobutyloxy)phenyl]-5-n-hexyl-pyrimidine is obtained.

Aufarbeitung

  1. temperatureunder reflux
  2. filtrationthe reaction mixture is filtered
  3. customthe residue is twice recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-40c7d00b92814a4fa5129238434cb585
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389290

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