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Methyl iodide → HCID 13712494, Verbindung

HRID 64969
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 64969
[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.CI.[C:22](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:22][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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 137124785-hydroxy-12H-benzo[a]phenothiazine

Produkt 1

HCID 13712494HCID 13712494, VerbindungAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

To a solution of 5-hydroxy-12H-benzo[a]phenothiazine (2.65 g) and methyl iodide (2.5 ml) in DMF (dimethylformamide) (10 ml) there was added powdered potassium carbonate (2.0 g). The mixture was stirred at room temperature and after 15 minutes, another addition of potassium carbonate (2.0 g) and methyl iodide (2.0 ml) was done. The mixture was stirred for a further 20 minutes, then it was diluted with ethyl acetate (100 ml and washed with water (60 ml) twice, dried and evaporated down. The residue was triturated with ether to afford solid crude product which was filtered (1.7 g). This crude product was chromatographed on a column of silica gel, eluting with dichloromethane to afford pure title compound (1.33 g), m.p. 168°-170° C.

Aufarbeitung

  1. stirringThe mixture was stirred for a further 20 minutes
  2. washwashed with water (60 ml) twice
  3. customdried
  4. customevaporated down
  5. customThe residue was triturated with ether
  6. customto afford solid crude product which
  7. filtrationwas filtered (1.7 g)
  8. customThis crude product was chromatographed on a column of silica gel
  9. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-c801a09080ee4a9b9ed80e4efb6baf6f
Quelldatensatz
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04611056

Notizen zur Reaktion

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