Sodium hydride → HCID 45790144, Verbindung

HRID 1912461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912461
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[CH:11]=[CH:10][NH:9][N:8]=1)=[O:6].[CH3:12][N:13]([CH3:18])[S:14](Cl)(=[O:16])=[O:15]>C1COCC1.O>[CH3:3][O:4][C:5]([C:7]1[CH:11]=[CH:10][N:9]([S:14](=[O:16])(=[O:15])[N:13]([CH3:18])[CH3:12])[N:8]=1)=[O:6]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 178498454HCID 178498454, Verbindung

Produkt 1

HCID 45790144HCID 45790144, VerbindungAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (1.57 g, 41.03 mmol) was added to a solution of 1H-pyrazole-3-carboxylic acid methyl ester (3.45 g, 27.36 mmol) in THF (20 mL) at 0° C. The mixture was stirred at 0° C. for 30 minutes. Then dimethylsulfamoyl chloride (4.41 mL, 41.03 mmol) was added and the mixture was allowed to warm to room temperature and stirred for 18 hours. The mixture was diluted with water and the product extracted with AcOEt. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to yield 1-dimethylsulfamoyl-1H-pyrazole-3-carboxylic acid methyl ester (4.8 g, 75% yield) as a colourless oil.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringstirred for 18 hours
  3. extractionthe product extracted with AcOEt
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvents evaporated in vacuo
  8. customThe crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 10/90)
  9. customThe desired fractions were collected
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-22e3623466c042f28356acbf719adcef
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609660B2

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