Hydrochloric Acid → 3,7-Dimethoxy-10-methylphenothiazine

HRID 2395126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2395126
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([S:14][C:15]=2[CH:16]=1)=[CH:12][C:11]([O:17][CH3:18])=[CH:10][CH:9]=3.[C:19](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.Cl>C1(C)C=CC=CC=1.COCCOCCN(CCOCCOC)CCOCCOC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH3:19])[C:8]3[C:13]([S:14][C:15]=2[CH:16]=1)=[CH:12][C:11]([O:17][CH3:18])=[CH:10][CH:9]=3

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 6211963,7-Dimethoxy-10H-phenothiazine

Produkt 1

HCID 189725343,7-Dimethoxy-10-methylphenothiazineAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-KatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A suspension of 21.75 g (83.9 mmol) of 3,7-dimethoxyphenothiazine, 43.36 g (0.34 mmol) of dried, powdered potassium carbonate, 25.22 g (0.20 mol) of dimethyl sulphate and 1.35 g (4.19 mmol) of tris-[2-(2-methoxyethoxy)ethyl]amine in 300 ml of toluene was stirred at 110° for 1 hour, then cooled and poured into 1 l of ice-water. The mixture was acidified slightly with 2N 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 ethanol/acetone, whereupon, after drying, 18.4 g (80.2%) of 3,7-dimethoxy-10-methylphenothiazine were obtained as a white solid of m.p. 166°-167°.

Aufarbeitung

  1. customof dried
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic phases were extracted with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was crystallized from ethanol/acetone, whereupon
  8. customafter drying

Quellen und Nachweise

ORD-Eintrag
ord-4a5400ce0b084649906c3dfb8cf933f0
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05811389

Notizen zur Reaktion

Wird geladen…