Isocyanatocarbonyl chloride → 1,3-Bis[4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy]benzene

HRID 263540

Reaktionsgleichung

Reaktionsgleichung von HRID 263540
[OH:1][NH:2][CH2:3][C:4]1[CH:26]=[CH:25][C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][NH:23][OH:24])=[CH:18][CH:17]=3)[CH:10]=2)=[CH:6][CH:5]=1.Cl[C:28]([N:30]=[C:31]=[O:32])=[O:29]>O1CCCC1>[O:29]=[C:28]1[NH:30][C:31](=[O:32])[O:24][N:23]1[CH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][C:7]3[CH:25]=[CH:26][C:4]([CH2:3][N:2]4[C:31](=[O:32])[NH:30][C:28](=[O:29])[O:1]4)=[CH:5][CH:6]=3)[CH:10]=2)=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 119708Isocyanatocarbonyl chlorideHCID 190384471,3-Bis[4-(N-hydroxyaminomethyl)phenoxy]benzene

Produkt 1

HCID 190384251,3-Bis[4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy]benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1,3-Bis[4-(N-hydroxyaminomethyl)phenoxy]benzene (0.704 g) was dissolved in 21 ml of tetrahydrofuran to which, with ice-cooling and in an atmosphere of argon, was subsequently added dropwise 0.354 ml of chlorocarbonyl isocyanate. After 10 minutes of stirring at the same temperature, the stirring was continued for 2 hours at room temperature. The solvent was evaporated under a reduced pressure, and the resulting residue was subjected to silica gel column chromatography to obtain 0.44 g of 1,3-bis[4-[(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy]benzene from fractions of chloroform-methanol (30:1) elution.

Aufarbeitung

  1. temperaturecooling and in an atmosphere of argon
  2. waitthe stirring was continued for 2 hours at room temperature
  3. customThe solvent was evaporated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6a994120ee8543678a81ec4fceb57f8f
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643931

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