Phosphorus oxychloride → 1-(2,4-difluorophenyl)-1-(4-(4-cyanothiazol-2-yl)-thiophen-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol

HRID 265332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 265332
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:17]1[S:18][CH:19]=[C:20]([C:22]2[S:23][CH:24]=[C:25]([C:27](=O)[NH2:28])[N:26]=2)[CH:21]=1)([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:17]1[S:18][CH:19]=[C:20]([C:22]2[S:23][CH:24]=[C:25]([C:27]#[N:28])[N:26]=2)[CH:21]=1)([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 190651561-(2,4-difluorophenyl)-1-(4-(4-carbamoylthiazol-2-yl)-thiophen-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol

Produkt 1

HCID 190651511-(2,4-difluorophenyl)-1-(4-(4-cyanothiazol-2-yl)-thiophen-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanolAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

1-(2,4-Difluorophenyl)-1-(4-(4-carbamoylthiazol-2-yl)-thiophen-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol (1.2 g) was dissolved in pyridine (7.1 ml). The solution was cooled on an ice bath, and phosphorus oxychloride (0.29 ml) was added thereto. The resultant mixture was stirred for 30 minutes. After the reaction, the reaction mixture was added with saline and extracted with ethyl acetate. An organic layer was washed once with 6N hydrochloric acid (20 ml) and then each once with water, a saturated aqueous solution of sodium hydrogencarbonate and saturated saline. After the thus-washed organic layer was dried over magnesium sulfate, the solvent was distilled out, and the residue was purified by chromatography on silica gel. Recrystallization from a solution of dichloromethane in ether was further conducted to obtain a solid (800 mg). Melting point: 172°-173° C.

Aufarbeitung

  1. temperatureThe solution was cooled on an ice bath
  2. customAfter the reaction
  3. additionthe reaction mixture was added with saline
  4. extractionextracted with ethyl acetate
  5. washAn organic layer was washed once with 6N hydrochloric acid (20 ml)
  6. dry with materialAfter the thus-washed organic layer was dried over magnesium sulfate
  7. distillationthe solvent was distilled out
  8. customthe residue was purified by chromatography on silica gel
  9. customRecrystallization from a solution of dichloromethane in ether

Quellen und Nachweise

ORD-Eintrag
ord-ad2797d1e92b43b9b22426ce11726976
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648372

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