Water → 4'-Methoxymethoxy-N-methyl-2'-nitro-p-toluenesulfonanilide

HRID 1356645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356645
[H-].[Na+].[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:23]=[CH:22][C:10]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[C:9]([N+:24]([O-:26])=[O:25])[CH:8]=1.S(OC)(O[CH3:31])(=O)=O.O>CN(C=O)C>[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:23]=[CH:22][C:10]([N:11]([CH3:31])[S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:14])=[O:13])=[C:9]([N+:24]([O-:26])=[O:25])[CH:8]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 185092944'-Methoxymethoxy-2'-nitro-p-toluenesulfonanilide

Produkt 1

HCID 185093144'-Methoxymethoxy-N-methyl-2'-nitro-p-toluenesulfonanilideAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (60%, 0.40 g (10.0 mmol)) in 15.0 ml of DMF, 4′-methoxymethoxy-2′-nitro-p-toluenesulfonanilide (3.00 g (8.51 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, dimethyl sulfate (1.0 ml (10.6 mmol)) was added and the mixture was stirred for 15 hours at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was then subjected to silica gel column chromatography with ethyl acetate-hexane (1:2) to give 2.91 g (93%) of the title compound as yellow crystals.

Aufarbeitung

  1. additionwas added
  2. stirringTo the resulting mixture, after 15 minutes' stirring at room temperature
  3. stirringthe mixture was stirred for 15 hours at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8f4f3a197df445de85c0dce07d6f3463
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586617B1

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