Chlorosulfonic acid → 4-(1-Methyl-1H-pyrazol-4-yl)benzene-1-sulfonyl chloride

HRID 1518192Notes

Reaction equation

HRID 1518192 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]=[N:3]1.[Cl:13][S:14](O)(=[O:16])=[O:15]>ClCCl>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([S:14]([Cl:13])(=[O:16])=[O:15])=[CH:11][CH:12]=2)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acid2×HCID 136924421-Methyl-4-phenyl-1H-pyrazole

Product 1

HCID 574944444-(1-Methyl-1H-pyrazol-4-yl)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.5 g of 1-methyl-4-phenyl-1H-pyrazole (3.16 mmol) were dissolved in 20 ml of dichloromethane. At 0° C., 0.232 ml of chlorosulfonic acid were added and the reaction mixture was stirred for 1 h under ice cooling. Additional 0.7 ml of chlorosulfonic acid were added, the mixture was stirred at 0° C. for 30 minutes and then 90 minutes at 50° C. The two phases were separated and the lower layer put on ice, extracted twice with diethyl ether, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to yield 0.496 g of the product.

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 minutes
  2. custom90 minutes
  3. customat 50° C
  4. customThe two phases were separated
  5. extractionextracted twice with diethyl ether
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-2517c2fc4eb3492c9a8859cb55dd0601
Source dataset
uspto-grants-2012_07
Patent number
US08232426B2

Reaction notes

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