Water → 10H-phenothiazin-2-ol

HRID 131101

Reaktionsgleichung

Reaktionsgleichung von HRID 131101
C[O:2][C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=1.[Cl-].[NH+]1C=CC=CC=1.O>C(OCC)(=O)C>[CH:4]1[C:5]2[NH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:13][C:14]=2[CH:15]=[CH:16][C:3]=1[OH:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 69401Einecs 211-027-4HCID 74490Methyl phenothiazin-2-yl ether

Produkt 1

HCID 1060871310H-phenothiazin-2-olAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of 25 g (109 mmol) of 2-methoxyphenothiazine and 60 g (4.8 eq.) of pyridinium chloride is heated at 170° C. for 15 hours. After cooling down to a temperature of approximately 80° C., the brown solution obtained is diluted with 200 ml of ethyl acetate. Stirring is maintained for 30 minutes before pouring the reaction mixture into 200 ml of water. After stirring and decantation, the organic phase is dried over sodium sulphate and concentrated to dryness, under vacuum. The greenish solid obtained is recrystallized from 700 ml of boiling toluene. An insoluble solid is eliminated by filtration, the filtrate crystallizes spontaneously overnight. The crystals are collected by filtration and rinsed using isopentane. After drying, 12.43 g of a grey solid is obtained with a yield of 53%. Melting point: 207-208° C.

Aufarbeitung

  1. temperatureAfter cooling down to a temperature of approximately 80° C.
  2. customthe brown solution obtained
  3. temperatureis maintained for 30 minutes
  4. stirringAfter stirring
  5. dry with materialdecantation, the organic phase is dried over sodium sulphate
  6. concentrationconcentrated to dryness, under vacuum
  7. customThe greenish solid obtained
  8. customis recrystallized from 700 ml of boiling toluene
  9. filtrationAn insoluble solid is eliminated by filtration
  10. customthe filtrate crystallizes spontaneously overnight
  11. filtrationThe crystals are collected by filtration
  12. washrinsed
  13. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-bfda4e5cfadb4994b4f0898525785a7d
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384933B2

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