Dimethylformamide → N,N,N',N'-Tetramethylazodicarboxamide

HRID 1490035

Reaktionsgleichung

Reaktionsgleichung von HRID 1490035
[Na+].[Na+].NC1C=C(S([O-])(=O)=O)C(C=CC2C(S([O-])(=O)=[O:20])=CC(N)=CC=2)=CC=1.OC1C(C(O)=O)=CC=C2[C:37]=1[N:36]=[CH:35]C=C2.ON1C2C=CC=C[C:45]=2[N:44]=[N:43]1.C1CCC(N=C=NC2CCCCC2)CC1.[CH3:66][N:67]([CH:69]=[O:70])[CH3:68]>>[CH3:66][N:67]([C:69]([N:43]=[N:44][C:45]([N:36]([CH3:35])[CH3:37])=[O:20])=[O:70])[CH3:68]

Komponenten

6

Edukt 5

HCID 6228Dimethylformamide2×HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 28374734,4'-diamino-2,2'-stilbenedisulfonic acid, disodium salt

Produkt 1

HCID 4278N,N,N',N'-Tetramethylazodicarboxamide

Versuchsvorschrift

To a solution of 4,4'-diaminostilbene-2,2'-disulfonic acid disodium salt (2.5 mmol, 1.036 g) in DMF (170 mL) a solution of 8-hydroxyquinoline-7-carboxylic acid (5.0mmol, 0.946 g) in DMF (140 mL) was added. To the mixture, 1-hydroxybenzotriazole (HBT) (6.0 mmol, 0.811 g) was added followed by 1,3-dicyclohexylcarbocilmide (DCC) (12.0 mmol, 2.476 g). The reaction mixture was stirred at room temperature for 6 days. Then, the solution was concentrated under reduced pressure. The precipitate was filtered off. The filtrate was evaporated in vacuo. To the residue, water and methanol (1:4) were added, and the pH was adjusted to 8. The insoluble material was filtered off, and the filtrate was evaporated under reduced pressure. The residue was extracted with choloroform (3×). The solid was collected by filtration, and treated with methanol. Insoluble material was filtered off and dried to give 0.8 g of pure, desired diamide. The methanol solution was used for fractionation on a Sephadex LH-20 column, with the eluent being methanol. This method allowed for the separation of an additional 0.59 g pure diamide (yield 73.5%) and traces of monoamide.

Aufarbeitung

  1. concentrationThen, the solution was concentrated under reduced pressure
  2. filtrationThe precipitate was filtered off
  3. customThe filtrate was evaporated in vacuo
  4. additionTo the residue, water and methanol (1:4) were added
  5. filtrationThe insoluble material was filtered off
  6. customthe filtrate was evaporated under reduced pressure
  7. extractionThe residue was extracted with choloroform (3×)
  8. filtrationThe solid was collected by filtration
  9. additiontreated with methanol
  10. filtrationInsoluble material was filtered off
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5f3f6f61a08e45c69689f183281fd906
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05681832

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