Acetonitrile → HCID 66711639, compound

HRID 1262328Notes

Reaction equation

HRID 1262328 reaction equation
[Br:1][C:2]1[C:3]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[N:4][N:5]([CH3:7])[CH:6]=1.[C:13](#N)C.C(=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>>[Br:1][C:2]1[C:3]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 66711987HCID 66711987, compound

Product 1

HCID 66711639HCID 66711639, compound

Conditions

Temperature
50 °C

Procedure

Into a 8-dram vial, N-(4-Bromo-1-methyl-1H-pyrazol-3-yl)-methanesulfonamide (1.38 g, 5.43 mmol), Acetonitrile (20 mL, 400 mmol), Potassium carbonate (1.50 g, 10.9 mmol), and Dimethyl sulfate (1.03 mL, 10.9 mmol) were added. The reaction mixture was heated at 50° C. overnight. The solid was filtered and washed DCM. The solvent was removed under vacuum to give a solid. The reaction mixture was purified via ISCO column chromatography with hexane and EtOAc as eluant. The collected fractions afforded N-(4-Bromo-1-methyl-1H-pyrazol-3-yl)-N-methyl-methanesulfonamide as a white solid (1.20 (82%).

Workup

  1. filtrationThe solid was filtered
  2. washwashed DCM
  3. customThe solvent was removed under vacuum
  4. customto give a solid
  5. customThe reaction mixture was purified via ISCO column chromatography with hexane and EtOAc as eluant

Sources & evidence

ORD record
ord-a7f5a50c8ea24b80be99ae536b60cca6
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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