Potassium Iodide → Diethyl 12H-benzo[a]phenothiazin-5-yl phosphate

HRID 2352224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2352224
[OH:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[C:12]([S:13]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=12.[P:20](Cl)([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(=O)([O-])[O-]>CN(C=O)C.C(OCC)(=O)C>[P:20]([O:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[C:12]([S:13]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=12)([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21]

Komponenten

8

Edukt 5

HCID 4875Potassium Iodide2×HCID 11430Potassium Carbonate2×HCID 13139Diethyl chlorophosphate2×HCID 19660Carbonate Ion2×HCID 137124785-hydroxy-12H-benzo[a]phenothiazine

Produkt 1

HCID 13712499Diethyl 12H-benzo[a]phenothiazin-5-yl phosphate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-hydroxy-12H-benzo[a]phenothiazine (1.5 g) and diethyl chlorophosphate (2 ml) in DMF (20 ml) there was added a powdered mixture of potassium carbonate (2 g) and potassium iodide (2 g). The reaction mixture was stirred at room temperature. After 30 minutes, a further addition of potassium carbonate and potassium iodide (2 g each) was made and stirring was continued. Two hours later more carbonate (2 g) and diethyl chlorophosphate (2 ml) were added, and then three hours later a final addition of carbonate (2 g) was made. The mixture was stirred for 3 days then diluted with ethyl acetate (60 ml) and the insolubles filtered. The filtrate was washed with water, dried and evaporated down. This residue was crystallized from acetone, then chromatographed on a column of silica gel, eluting first with 1:1, then 3:1 mixtures of ethyl acetate and hexane to afford pure title compound (337 mg), m.p. 162°-163° C.

Aufarbeitung

  1. stirringstirring
  2. stirringThe mixture was stirred for 3 days
  3. filtrationthe insolubles filtered
  4. washThe filtrate was washed with water
  5. customdried
  6. customevaporated down
  7. customThis residue was crystallized from acetone
  8. customchromatographed on a column of silica gel
  9. washeluting first with 1:1

Quellen und Nachweise

ORD-Eintrag
ord-a757ce851cb34d11add3bae48c17825f
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04876246

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