Dabco → HCID 67958277, compound

HRID 2369593Notes

Reaction equation

HRID 2369593 reaction equation
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]

Participants

6

Reactant 3

HCID 9237DabcoHCID 83372Dimethylsulphamoyl chlorideHCID 178469067HCID 178469067, compound

Product 1

HCID 67958277HCID 67958277, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e4a98de59dd349cca55479fdc0ce8560
Source dataset
uspto-grants-2014_04
Patent number
US08703946B2

Reaction notes

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