Phosphorus oxychloride → 2-Chloro-5-methyl-1,3-benzoxazole

HRID 563719

Reaktionsgleichung

Reaktionsgleichung von HRID 563719
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](S)=[N:7][C:6]=2[CH:11]=1.P(Cl)(Cl)([Cl:14])=O.P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[Cl:14][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:11][C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178423563HCID 178423563, Verbindung

Produkt 1

HCID 99896072-Chloro-5-methyl-1,3-benzoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Methyl-benzooxazole-2-thiol (5.0 g, 30.2 mmol), phosphorus oxychloride (25.0 mL, 269.4 mmol), and phosphorus pentachloride (7.56 g, 36.3 mmol) were combined in CH2Cl2 (30 mL), and the reaction was stirred at room temperature overnight. The mixture was concentrated several times from fresh CH2Cl2 to remove traces of phosphorus oxychloride, and the residue was treated with saturated aqueous Na2CO3 to adjust to pH 8. The aqueous layer was extracted twice with CH2Cl2, and the combined organic layers were washed with H2O and brine, and then dried over Na2SO4, decanted, and concentrated. The crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound.

Aufarbeitung

  1. concentrationThe mixture was concentrated several times from fresh CH2Cl2
  2. customto remove traces of phosphorus oxychloride
  3. additionthe residue was treated with saturated aqueous Na2CO3
  4. extractionThe aqueous layer was extracted twice with CH2Cl2
  5. washthe combined organic layers were washed with H2O and brine
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated
  9. customThe crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-35365d21e69b463cb7e461ec1face7ed
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067445B2

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