Ammonium Hydroxide → 1,3-dimethyl-1H-pyrazole-4-sulfonamide

HRID 331054Notes

Reaction equation

HRID 331054 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([S:7](Cl)(=[O:9])=[O:8])[C:4]([CH3:11])=[N:3]1.[OH-].[NH4+:13]>C1COCC1>[CH3:1][N:2]1[CH:6]=[C:5]([S:7]([NH2:13])(=[O:9])=[O:8])[C:4]([CH3:11])=[N:3]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 46357071,3-dimethyl-1H-pyrazole-4-sulfonyl chloride

Product 1

HCID 133427831,3-dimethyl-1H-pyrazole-4-sulfonamideYield 111.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,3-dimethyl-1H-pyrazole-4-sulfonyl chloride (232 mg, 1.192 mmol) in THF (10.0 mL) was cooled to 0° C. and to it was added dropwise ammonium hydroxide (0.650 mL, 16.69 mmol). The reaction mixture was allowed to warm to RT and left to stir over the weekend (ca. 64 hours). The reaction mixture was concentrated in vacuo. The residues were taken up in water, then neutralized with 1M aqueous HCl (dropwise addition) to pH 5-6 and extracted with ethyl acetate (3×50 mL). The combined organics were dried over MgSO4, filtered and evaporated to dryness, producing the title compound (233 mg). LCMS (A): m/z (M+H)+ 176, C5H9N3O2S requires 175 (acidic).

Workup

  1. waitleft
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondropwise addition) to pH 5-6
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organics were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-6d52788399694fb69f0a848ce112f179
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

Loading…