Benzyl Bromide → 1-Benzyl-6-methyl-isatoic anhydride

HRID 1646206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1646206
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[NH:12][C:11](=[O:13])[O:10][C:8](=[O:9])[C:7]=12.[H-].[Na+].[H][H].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:18]([C:7]12[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][CH:6]1[NH:12][C:11](=[O:13])[O:10][C:8]2=[O:9])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 867464321-Benzyl-6-methyl-isatoic anhydride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of 6-methyl-isatoic anhydride (4.5 gm) in DMF (30 ml) was added dropwise to a stirred suspension of 60% sodium hydride (1.0 gm) in DMF (20 ml) under nitrogen atmosphere. The reaction was then warmed to 45° and stirred until hydrogen evolution ceased. It was then cooled and a solution of benzyl bromide (4.4 gm) in DMF (10 ml) was added slowly. Stirring was continued for one hour at room temperature and the solution was then evaporated under reduced pressure at 45° C. The resulting solid was suspended in methylene chloride, the insoluble inorganic solid was removed by filtration and the filtrate was evaporated to afford the title compound as a crystalline solid.

Aufarbeitung

  1. temperatureThe reaction was then warmed to 45°
  2. temperatureIt was then cooled
  3. customthe solution was then evaporated under reduced pressure at 45° C
  4. customthe insoluble inorganic solid was removed by filtration
  5. customthe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-274146fd290d45be91e3bdc43dd2e0d0
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05179093

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