Methanol → 1-methanesulfonylmethyl-3-nitro-1H-pyrazole

HRID 546015Notes

Reaction equation

HRID 546015 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].CS[CH2:9][N:10]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[N:11]1.[CH3:18]O>O>[CH3:18][S:3]([CH2:9][N:10]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[N:11]1)(=[O:5])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 671906581-methylsulfanylmethyl-3-nitro-1H-pyrazole

Product 1

HCID 671889651-methanesulfonylmethyl-3-nitro-1H-pyrazoleYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Oxone (2.05 g, 3.36 mmol) was added to a mixture of 1-methylsulfanylmethyl-3-nitro-1H-pyrazole (194 mg, 1.12 mmol) in methanol (10 mL) and deionized water (100 μL) was allowed to proceed for 16 h with vigorous stirring. The solvent was removed in vacuo and the crude material was purified by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 10 g; 0% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded 1-methanesulfonylmethyl-3-nitro-1H-pyrazole as a white solid (184 mg, 80%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude material was purified by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 10 g; 0% ethyl acetate/hexanes to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-56903b4f1b0e46bcb31c03c0654946db
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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