Chlorosulfonic acid → 1-methyl-1H-pyrazole-4-sulfonyl chloride

HRID 553498Notes

Reaction equation

HRID 553498 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.[Cl:7][S:8](O)(=[O:10])=[O:9]>>[CH3:1][N:2]1[CH:6]=[C:5]([S:8]([Cl:7])(=[O:10])=[O:9])[CH:4]=[N:3]1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 702551H-Pyrazole, 1-methyl-

Product 1

HCID 170247301-methyl-1H-pyrazole-4-sulfonyl chloride

Conditions

Temperature
0 °C

Procedure

Add 1-methyl-1H-pyrazole (100 g, 1.18 mol) dropwise to chlorosulfonic acid (325 mL, 4.84 mol) stirring at 0° C. under nitrogen atmosphere. Heat reaction mixture at 110° C. for 3 hr. Cool to room temperature, then pour carefully into crushed ice with stirring. Recover the resulting white solid by vacuum filtration, wash with water, and dry under vacuum. Use the resulting material (72.2 g, 33%) without further purification.

Workup

  1. temperatureHeat
  2. customreaction mixture at 110° C. for 3 hr
  3. temperatureCool to room temperature
  4. additionpour carefully
  5. custominto crushed ice
  6. stirringwith stirring
  7. customRecover the resulting white solid
  8. filtrationby vacuum filtration
  9. washwash with water
  10. customdry under vacuum
  11. customwithout further purification

Sources & evidence

ORD record
ord-3dacf246f8404fb2a1386eb59c51b86f
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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