Dimethylformamide → 3,7-Diformyl-10-p-tolylphenothiazine

HRID 2287296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2287296
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([N:7]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[S:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:3][CH:2]=1.CN([CH:25]=[O:26])C.P(Cl)(Cl)(Cl)=O.[C:32](=O)([O-])[O-:33].[Na+].[Na+]>[Cl-].[Zn+2].[Cl-].O.C1(C)C=CC=CC=1>[CH:32]([C:17]1[CH:18]=[CH:19][C:20]2[N:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:21])=[CH:6][CH:5]=3)[C:8]3[C:13]([S:14][C:15]=2[CH:16]=1)=[CH:12][C:11]([CH:25]=[O:26])=[CH:10][CH:9]=3)=[O:33]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 172985110-(4-Methylphenyl)phenothiazine

Produkt 1

HCID 187044763,7-Diformyl-10-p-tolylphenothiazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To 200 ml of toluene were added 20.0 g (69.1 mmol) of 10-p-tolylphenothiazine (4b), 10.0 g (73.4 mmol) of zinc chloride, and 22 ml (284.1 mmol) of DMF. The mixture was stirred, and 27 ml (289.7 mmol) of phosphorus oxychloride was gradually added thereto dropwise. The resultant mixture was reacted at 80° C. for 3 days and then poured into 300 ml of water. This mixture was neutralized with sodium carbonate, stirred at 80° C. for 2 hours, and then subjected to liquid separation. The aqueous phase was extracted with toluene three times, and the resultant organic phase collected was dried (with MgSO4) and concentrated. The residue was recrystallized twice from ethyl acetate to obtain 8.59 g of the target compound.

Aufarbeitung

  1. stirringstirred at 80° C. for 2 hours
  2. customsubjected to liquid separation
  3. extractionThe aqueous phase was extracted with toluene three times
  4. customthe resultant organic phase collected
  5. dry with materialwas dried (with MgSO4)
  6. concentrationconcentrated
  7. customThe residue was recrystallized twice from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-36c94a179c3343b7be10bef66f6524e1
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06083651

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