Phosphorus oxychloride → 3-Benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

HRID 636380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636380
[C:1]1([S:7]([C:10]2[C:11]([S:21][CH3:22])=[N:12][N:13]3[C:18](O)=[CH:17][C:16]([CH3:20])=[N:15][C:14]=23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:25]>>[C:1]1([S:7]([C:10]2[C:11]([S:21][CH3:22])=[N:12][N:13]3[C:18]([Cl:25])=[CH:17][C:16]([CH3:20])=[N:15][C:14]=23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178503606HCID 178503606, Verbindung

Produkt 1

HCID 109810973-Benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidineAusbeute 94 %

Versuchsvorschrift

A suspension of 3.0 g (8.94 mmol) of 3-benzenesulphonyl-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ol in 20 ml of POCl3 was heated at reflux for 45 min. The reaction solution was cooled to RT and evaporated in a high vacuum. The residue was treated with 100 ml of ice-water and the pH value of the solution was adjusted to 8 with sat. NaHCO3 solution. The aqueous phase was extracted three times with 100 ml of CH2Cl2, and the organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/AcOEt 19:1) of the residue yielded 3.0 g (94%) of 3-benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine as pale yellow crystals, m.p. 163-165° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 45 min
  3. customevaporated in a high vacuum
  4. additionThe residue was treated with 100 ml of ice-water
  5. extractionThe aqueous phase was extracted three times with 100 ml of CH2Cl2
  6. dry with materialthe organic phases were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-072e279a76dd4cf6afa00c8d00a7271e
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194410B1

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