Dabco → HCID 67958277, Verbindung

HRID 1773783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773783
N12CCN(CC1)CC2.[CH3:9][N:10]([CH3:15])[S:11](Cl)(=[O:13])=[O:12].[CH2:16]([O:18][C:19]([C:21]1[NH:22][N:23]=[C:24]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)=[O:20])[CH3:17]>CC#N.O>[CH2:16]([O:18][C:19]([C:21]1[N:22]([S:11](=[O:13])(=[O:12])[N:10]([CH3:15])[CH3:9])[N:23]=[C:24]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)=[O:20])[CH3:17]

Komponenten

6

Edukt 3

HCID 9237DabcoHCID 83372Dimethylsulphamoyl chlorideHCID 178469067HCID 178469067, Verbindung

Produkt 1

HCID 67958277HCID 67958277, VerbindungAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1,4-Diazabicylo[2.2.2]octane (1.0 g, 8.93 mmol) and dimethylsulfamoyl chloride (0.88 mL, 8.2 mmol) were sequentially added to a solution of 5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (2.0 g, 8.12 mmol) in CH3CN (10 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 18 hours. The mixture was diluted with H2O and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents concentrated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 40/60). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (2.42 g, 84% yield) as a white solid.

Aufarbeitung

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe solvents concentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 40/60)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ff67327f069c4ddd923a9e9a7744028c
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255103B2

Notizen zur Reaktion

Wird geladen…