Chloromethyl methyl sulfide → 1-methylsulfanylmethyl-3-nitro-1H-pyrazole

HRID 546014Notes

Reaction equation

HRID 546014 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[H-].[Na+].Cl[CH2:12][S:13][CH3:14]>CN(C)C=O>[CH3:12][S:13][CH2:14][N:6]1[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]1

Participants

5

Reactant 3

HCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 178526745HCID 178526745, compound

Product 1

HCID 671906581-methylsulfanylmethyl-3-nitro-1H-pyrazoleYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-nitro-1H-pyrazole (prepared in example 3, 50 mg, 4.42 mmol) in anhydrous N,N-dimethylformamide (5 mL), a 60% dispersion of sodium hydride in mineral oil (230 mg, 5.75 mmol) was added while stirring under nitrogen. After the effervescence ceased and the mixture was stirred for additional 30 min, chloro-methylsulfanyl-methane (555 mg, 5.75 mmol) was added. The mixture was continued to stir under nitrogen for an additional 2 h. The solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded 1-methylsulfanylmethyl-3-nitro-1H-pyrazole (514 mg, 67%) as a white solid.

Workup

  1. stirringthe mixture was stirred for additional 30 min
  2. stirringto stir under nitrogen for an additional 2 h
  3. customThe solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% ethyl acetate/hexanes to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d2c2da2a1c9444aa9596b93435cc7ac7
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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