Hydroxyamine hydrochloride → N-{4-[1-(hydroxyamino)ethylidene]cyclohexa-2,5-dien-1-ylidene}methanesulfonamide

HRID 238930

Reaktionsgleichung

Reaktionsgleichung von HRID 238930
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[CH3:13])=[CH:8][CH:7]=1)(=[O:4])=[O:3].Cl.[NH2:16][OH:17]>N1C=CC=CC=1.O>[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[N:16][OH:17])[CH3:13])=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Komponenten

5

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 684083N-(4-acetylphenyl)methanesulfonamide

Produkt 1

HCID 6612326N-{4-[1-(hydroxyamino)ethylidene]cyclohexa-2,5-dien-1-ylidene}methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 4′-(Methylsulfonylamino)acetophenone (13-5, 5 mmol) and hydroxylamine hydrochloride (0.695 g, 10 mmol) in pyridine (5 mL) was heated at 70° C. for 3 h. The reaction mixture was cooled to room temperature, diluted with H2O, and extracted with EtOAc several times. The combined organic layers were washed with H2O and brine, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:1) as eluant to 4′-Methylsulfonylamino)acetophenone oxime (13-8, LJO-299).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc several times
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8be3c1feb80d41cca7259ae6441eb595
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642657B2

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