Dimethylformamide → HCID 59249334, compound

HRID 1807218Notes

Reaction equation

HRID 1807218 reaction equation
[CH3:1][C:2]([OH:13])([CH3:12])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[N:5]1.CN(C=O)C.[H-].[Na+].[C:21]([O:24][CH2:25][CH3:26])(=O)C>[NH4+].[Cl-]>[CH3:12][C:2]([O:13][CH2:26][C@@H:25]1[CH2:21][O:24]1)([CH3:1])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[N:5]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 545944402-methyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-ol

Product 1

HCID 59249334HCID 59249334, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-methyl-1-(3-nitro-pyrazol-1-yl)-propan-2-ol (0.64 g, 3.46 mmol), and DMF (30 mL) was stirred at 0° C. for 5 min, then NaH (60% dispersion in oil, 0.415 g, 17.3 mmol) was added and stirred 20 min at 0° C. S-(+)-glycidyl-3-nitrobenzenesulfonate (1.79 g, 6.92 mmol) was added and stirred at 0° C. for 1 h then warmed to 25° C. for 3 h. The mixture was then diluted with NH4Cl(s), ethyl acetate, the organic phase was separated, washed with NaHCO3(satd) dried with Na2SO4, and filtered. The mixture was then concentrated and purified by column chromatography (40-120 g Analogix column, 80% EtOAc/heptane to yield the product 1-[2-methyl-2-((S)-1-oxiranylmethoxy)-propyl]-3-nitro-1H-pyrazole as a white solid (0.36 g, 43.1%).

Workup

  1. stirringstirred 20 min at 0° C
  2. stirringstirred at 0° C. for 1 h
  3. temperaturethen warmed to 25° C. for 3 h
  4. customthe organic phase was separated
  5. washwashed with NaHCO3(satd)
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationThe mixture was then concentrated
  9. custompurified by column chromatography (40-120 g Analogix column, 80% EtOAc/heptane

Sources & evidence

ORD record
ord-8a6b0cc609194b94a191548088dd8981
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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