Water → 3-Phenyl-2-[(4-methylpyridin-2-yl)methylthio]-4(3H)-quinazolinone

HRID 1085065

Reaktionsgleichung

Reaktionsgleichung von HRID 1085065
C[O-].[Na+].[SH:4][C:5]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13](=[O:21])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1.Cl.Cl[CH2:24][C:25]1[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=1.O>CO>[C:15]1([N:14]2[C:13](=[O:21])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]=[C:5]2[S:4][CH2:24][C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10942334Sodium MethoxideHCID 200610712-(Chloromethyl)-4-methylpyridine hydrochlorideHCID 178515047HCID 178515047, Verbindung

Produkt 1

HCID 145751693-Phenyl-2-[(4-methylpyridin-2-yl)methylthio]-4(3H)-quinazolinoneAusbeute 30,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

8.7 ml of 28% methanolic solution of sodium methoxide were added to a solution of 5.0 g of 2-mercapto-3-phenyl-4(3H)-quinazolinone and 4.0 g of 2-chloromethyl-4-methylpyridine hydrochloride in methanol, and the stirring was continued at room temperature for 5 hours. The reaction solution was poured into water and extracted with chloroform. The chloroform layer was washed with an aqueous solution of sodium carbonate and dried over sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography. The fraction eluted with 8% ethyl acetate in chloroform was collected and crystallized from ethyl acetate to give 2.17 g (30.7%) of the title compound.

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with an aqueous solution of sodium carbonate
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography
  6. washThe fraction eluted with 8% ethyl acetate in chloroform
  7. customwas collected
  8. customcrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-650ced8df29c4ed4af120a116f7fb3c1
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05008266

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