Dimethylformamide → 2-methyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-ol

HRID 1807095Notes

Reaction equation

HRID 1807095 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[CH3:9][C:10]1([CH3:13])[CH2:12][O:11]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(OCC)(=O)C.O>[CH3:9][C:10]([OH:11])([CH3:13])[CH2:12][N:6]1[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 178526745HCID 178526745, compound

Product 1

HCID 545944402-methyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-nitro-1H-pyrazole (10.0 g, 88.43 mmol), 2,2-dimethyl-oxirane (15.7 mL, 176.9 mmol), potassium carbonate (18.2 g, 132 mmol) and DMF (100 mL) was stirred at 100° C. for 1 h, then stirred ON at rt. The mixture was then diluted with ethyl acetate and water, the organic layer was separated, dried over Na2SO4, and filtered. The resulting mixture was concentrated under reduced pressure to yield the crude product that was purified (50% EtOAc/heptane) to yield the product 2-methyl-1-(3-nitro-pyrazol-1-yl)-propan-2-ol as a waxy solid (4.88 g, 30%).

Workup

  1. stirringstirred ON at rt
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe resulting mixture was concentrated under reduced pressure
  6. customto yield the crude product that
  7. customwas purified (50% EtOAc/heptane)

Sources & evidence

ORD record
ord-81cf5276a2194192b3617f5ff804673c
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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