Sodium Dithionite → 4-bromo-2,7-dimethoxy-3-hydroxy-10H-phenothiazine

HRID 979309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 979309
[Br:1][C:2]1[C:3](=[O:20])[C:4]([O:18][CH3:19])=[CH:5][C:6]2[C:15]=1[S:14][C:13]1[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=1)[N:7]=2.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.O>[Br:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=3)[NH:7][C:6]=2[CH:5]=[C:4]([O:18][CH3:19])[C:3]=1[OH:20]

Komponenten

5

Edukt 2

HCID 24489Sodium DithioniteHCID 1221824-Bromo-2,7-dimethoxy-3H-phenothiazin-3-one

Produkt 1

HCID 138537384-bromo-2,7-dimethoxy-3-hydroxy-10H-phenothiazineAusbeute 129,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 4-bromo-2,7-dimethoxy-3H-phenothiazin-3-one (100 g) in a mixture of ethyl acetate (2 l) and water (1 l) was added sodium hydrosulfite (200 g) in one batch with mechanical stirring. The orange reaction mixture was stirred for 15 hours under a nitrogen atmosphere. The resulting white reaction mixture was filtered and the precipitate washed with water under a nitrogen atmosphere to prevent air oxidation of the compound. The title compound (130 g) was obtained as a wet material and was used as such in the next step (Step 2). An analytical sample was air dried, m.p. 185° C.

Aufarbeitung

  1. filtrationThe resulting white reaction mixture was filtered
  2. washthe precipitate washed with water under a nitrogen atmosphere

Quellen und Nachweise

ORD-Eintrag
ord-910e31368f7841b597278a48f33dfee3
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04667032

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