Sodium hydride → N,N,2-trimethyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-amine

HRID 1844538Notes

Reaction equation

HRID 1844538 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:10]=[CH:9][NH:8][N:7]=1)([O-:5])=[O:4].Cl[CH2:12][C:13]([CH3:18])([N:15]([CH3:17])[CH3:16])[CH3:14].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[CH3:16][N:15]([CH3:17])[C:13]([CH3:18])([CH3:14])[CH2:12][N:8]1[CH:9]=[CH:10][C:6]([N+:3]([O-:5])=[O:4])=[N:7]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 148217101-chloro-N,N,2-trimethylpropan-2-amineHCID 178526745HCID 178526745, compound

Product 1

HCID 66880823N,N,2-trimethyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-amine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (156 mg) was added to a solution of 3-nitro-1H-pyrazole (196 mg) in anhydrous DMF (2 mL) under cooling with ice, and the mixture was stirred at room temperature for 15 minutes. A solution of 1-chloro-N,N,2-trimethylpropan-2-amine in DMF (0.52 mL) was added to the resultant mixture, and the mixture was stirred at room temperature for about 24 hours. A saturated aqueous ammonium chloride solution (25 mL) and ethyl acetate (25 mL) were added to the reaction mixture and stirred under cooling with ice. The organic layer was separated, washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and filtrated, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (neutral spherical silica gel, ethyl acetate:hexane=1:1) to give N,N,2-trimethyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-amine as yellow powder crystals (90.9 mg, yield: 25%).

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at room temperature for about 24 hours
  3. stirringstirred
  4. temperatureunder cooling with ice
  5. customThe organic layer was separated
  6. washwashed with saturated brine (100 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltrated
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (neutral spherical silica gel, ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-9ff686d7ad90405d9e00f755e34dd044
Source dataset
uspto-grants-2015_02
Patent number
US08946440B2

Reaction notes

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