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

HRID 263541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 263541
[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.C(O[C:32]([N:34]=[C:35]=[O:36])=[O:33])CCC.[OH-:37].[Na+].Cl>O1CCCC1>[O:37]=[C:35]1[NH:34][C:32](=[O:33])[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:35](=[O:36])[NH:34][C:32](=[O:33])[O:1]4)=[CH:5][CH:6]=3)[CH:10]=2)=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12538171Butyloxycarbonyl isocyanateHCID 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 (1.76 g) was dissolved in 35 ml of tetrahydrofuran to which, with ice-cooling and in an atmosphere of argon, was subsequently added dropwise 1.65 g of n-butoxycarbonyl isocyanate. After 30 minutes of stirring at the same temperature, 1N sodium hydroxide aqueous solution was added dropwise thereto and the stirring was continued for 30 minutes at room temperature. After adding 1N hydrochloric acid, the solvent was evaporated, and the resulting residue was subjected to silica gel column chromatography to obtain 1.0 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. additionwas added dropwise
  3. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6fe3986684ff49c8bc654087af1a8eae
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643931

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