Hydrochloric Acid → 3,7-Dimethoxy-10-methyl-phenothiazine-4-carbaldehyde

HRID 2395174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2395174
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH3:24])[C:13]3[C:18]([S:19][C:20]=2[CH:21]=1)=[CH:17][C:16]([O:22][CH3:23])=[CH:15][CH:14]=3.[CH:25](N1CCCCC1)=[O:26].Cl>C(OCC)C.O1CCCC1>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH3:24])[C:13]3[C:18]([S:19][C:20]=2[C:21]=1[CH:25]=[O:26])=[CH:17][C:16]([O:22][CH3:23])=[CH:15][CH:14]=3

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 174291-PiperidinecarboxaldehydeHCID 189725343,7-Dimethoxy-10-methylphenothiazineHCID 178418339Butyllithium

Produkt 1

HCID 189725603,7-Dimethoxy-10-methyl-phenothiazine-4-carbaldehydeAusbeute 179,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21868444Ether tetrahydrofuranLösungsmittel

Versuchsvorschrift

16.25 ml of n-butyllithium solution (1.6M in hexane) were added dropwise at -78° under argon to a solution of 5.46 g (10.0 mmol) of 3,7-dimethoxy-10-methylphenothiazine in 100 ml of diethyl ether/tetrahydrofuran (4:1). The reaction mixture was stirred at -70° for 15 minutes, brought slowly to 0°, stirred for 2 hours and then treated at 0° with 3.39 g (30.0 mmol) of N-formylpiperidine. After stirring at 0° for 2 hours the mixture was poured into 500 ml of ice-water, whereupon it was acidified slightly with 0.5N hydrochloric acid solution and extracted with ethyl acetate. The combined organic phases were extracted with saturated sodium chloride solution, dried over magnesium sulphate and evaporated. The residue was crystallized from acetone, whereupon, after drying, 5.42 g (90%) of 3,7-dimethoxy-10-methyl-phenothiazine-4-carbaldehyde were obtained as a red solid of m.p. 150°.

Aufarbeitung

  1. custombrought slowly to 0°
  2. stirringstirred for 2 hours
  3. stirringAfter stirring at 0° for 2 hours the mixture
  4. extractionextracted with ethyl acetate
  5. extractionThe combined organic phases were extracted with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue was crystallized from acetone, whereupon
  9. customafter drying

Quellen und Nachweise

ORD-Eintrag
ord-e857d6f504f7437fa9a5864cd387e234
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05811548

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