Water → HCID 178440789, Verbindung

HRID 1078206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1078206
[C:1]([C:5]1[CH:6]=[C:7]([CH:23]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=1[OH:26])[CH:8]=[C:9]1[C:14](=[O:15])[N:13]([CH2:16][C:17]#[N:18])[C:12]2[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=2[S:10]1)([CH3:4])([CH3:3])[CH3:2].[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+].O>CC(C)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:23]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=1[OH:26])[CH:8]=[C:9]1[C:14](=[O:15])[N:13]([CH2:16][C:17]2[NH:33][N:32]=[N:31][N:18]=2)[C:12]2[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=2[S:10]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 54061185HCID 54061185, Verbindung

Produkt 1

HCID 178440789HCID 178440789, VerbindungAusbeute 56,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To a solution of 2-(3,5-di-tert.-butyl-4-hydroxybenzylidene) -4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazine (compound No. 1-1, 0.335 g) in dimethylformaldehyde (5 ml), sodium azide (0.078 g) and ammonium chloride (0.064 g) were added. The mixture was stirred overnight at 105° C. under a nitrogen atmosphere. To the mixture, water was added, and the whole was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. To the oily residue, 1N aqueous sodium hydroxide solution was added. The mixture was washed with diethyl ether, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 0.21 g (56.9%) of the titled compound.

Aufarbeitung

  1. extractionthe whole was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. additionTo the oily residue, 1N aqueous sodium hydroxide solution was added
  5. washThe mixture was washed with diethyl ether
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe oily residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4abd2381923847feab648a528e381c46
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05547952

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