Butyl iodide → HCID 67190679, compound

HRID 546054Notes

Reaction equation

HRID 546054 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[H-].[Na+].I[CH2:12][CH2:13][CH2:14][CH3:15]>CN(C)C=O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:12][CH2:13][CH2:14][CH3:15])[N:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 178526745HCID 178526745, compound

Product 1

HCID 67190679HCID 67190679, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Nitro-1H-pyrazole (prepared in example 3, 100 mg, 0.89 mmol) was dissolved in anhydrous N,N-dimethylformamide (4 mL) and a 60% dispersion of sodium hydride in mineral oil (42 mg, 1.06 mmol) was added while stirring under nitrogen. After the effervescence ceased and the reaction stirred for an additional 10 min before 1-iodo-butane (121 μL, 1.06 mmol) was added. The reaction continued to stir under nitrogen for 4 h. The reaction was stored at −25° C. for 16 h. The solution was diluted with ethyl acetate (30 mL), washed with water (2×10 mL), saturated aqueous brine solution (10 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 25% ethyl acetate/hexanes to 75% ethyl acetate/hexanes) afforded 3-nitro-1-butyl-1H-pyrazole (111 mg, 62%) as a clear oil.

Workup

  1. additionwas added
  2. stirringto stir under nitrogen for 4 h
  3. washwashed with water (2×10 mL), saturated aqueous brine solution (10 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 25% ethyl acetate/hexanes to 75% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-afb26ccdb6534710af8380a3f189fbd7
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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