Water → N-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)methanesulfonamide

HRID 714903Notes

Reaction equation

HRID 714903 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[N:7][N:8]([CH2:10][CH2:11][NH2:12])[CH:9]=1)([O-:4])=[O:3].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].O>O1CCCC1>[N+:2]([C:5]1[CH:6]=[N:7][N:8]([CH2:10][CH2:11][NH:12][S:21]([CH3:20])(=[O:23])=[O:22])[CH:9]=1)([O-:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 717566062-(4-nitro-1H-pyrazol-1-yl)ethan-1-amine hydrochloride

Product 1

HCID 117840477N-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-nitro-1H-pyrazol-1-yl)ethanamine hydrochloride (1.0 g) obtained in Step B of Example 348 in tetrahydrofuran (30 mL) were added triethylamine (2.2 mL) and methanesulfonyl chloride (0.60 mL) in an ice bath, and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized (hexane/ethyl acetate) to give the title compound (880 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d045afa469744c87b53664a457eac322
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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