Ammonia → 1,3-dimethyl-1H-pyrazole-4-sulfonamide

HRID 2106564Notes

Reaction equation

HRID 2106564 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH3:7])=[N:3]1.Cl[S:9]([OH:12])(=O)=[O:10].[NH3:13].O>CCOCC>[CH3:1][N:2]1[CH:6]=[C:5]([S:9]([NH2:13])(=[O:12])=[O:10])[C:4]([CH3:7])=[N:3]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 24638Chlorosulfonic acidHCID 790961H-Pyrazole, 1,3-dimethyl-

Product 1

HCID 133427831,3-dimethyl-1H-pyrazole-4-sulfonamideYield 19,024.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
90 °C

Procedure

59 g (0.615 mmol) of 1,3-dimethylpyrazole is added slowly to 300 g (2.5 mmol) of chlorosulfonic acid at 0° C. The reaction is warmed to 90° C. for 3 hours, cooled and poured onto 500 g of ice. The aqueous solution is extracted with 3×100 ml of ether. The organic extract is dried over anhydrous sodium sulfate and filtered. The ether solution is added dropwise to a solution of 55 grams of anhydrous ammonia (2.5 mmol) in 250 ml of ether. After standing overnight, water is added and the layers separated. The aqueous solution is extracted with ethyl acetate, the organic solutions combined and dried over anhydrous sodium sulfate. After removal of the drying agent, the solvent is removed in vacuo giving 20.5 g of product, m.p. =97°-105° C.

Workup

  1. temperaturecooled
  2. extractionThe aqueous solution is extracted with 3×100 ml of ether
  3. extractionThe organic extract
  4. dry with materialis dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe layers separated
  7. extractionThe aqueous solution is extracted with ethyl acetate
  8. dry with materialdried over anhydrous sodium sulfate
  9. customAfter removal of the drying agent
  10. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-c1b9c6229d704af0810528207d67f993
Source dataset
uspto-grants-1990_06
Patent number
US04931081

Reaction notes

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