Water → HCID 18172536, Verbindung

HRID 1061107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1061107
[N:1](OCCCC)=[O:2].[C:8]1([N:14]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:15](=[O:28])[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:18](C)[C:17]=2[CH3:27])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC(C)([O-])C.[K+].O>CN(C)C=O.C(O)(=O)C>[C:8]1([N:14]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:15](=[O:28])[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:18]([NH:1][OH:2])[C:17]=2[CH3:27])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10996Butyl nitriteHCID 18757278HCID 18757278, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 18172536HCID 18172536, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 0.7 g (6.9 mmol) of n-butyl nitrite (97%) and 2 g (5.3 mmol) of N,N-diphenyl-2,3-dimethyl-4-methylsulfonyl-benzamide in 30 ml of dimethylformamide is cooled to from −55 to −60° C., and a solution of 1.4 g (12 mmol) of potassium tert-butoxide in 10 ml of dimethylformamide is added dropwise at this temperature, over a period of 20 minutes. The reaction is monitored by HPLC. For work-up, initially 10 ml of water are added, and the mixture is then adjusted to pH 5-6 using glacial acetic acid. The mixture is then poured onto 100 ml of ice-water and the aqueous phase is extracted with ethyl acetate. The organic phase is washed with sodium bicarbonate solution, dried over magnesium sulfate and concentrated. This gives 3.0 g of a partially crystalline crude product, which is purified by silica gel chromatography using the mobile phase toluene/acetone.

Aufarbeitung

  1. extractionthe aqueous phase is extracted with ethyl acetate
  2. washThe organic phase is washed with sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThis gives 3.0 g of a partially crystalline crude product, which is purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-994a18feadd6447786749bbd5b2e868a
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525204B1

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