Phenethyl bromide → 3-Nitro-1-(2-phenylethyl)-1H-pyrazole

HRID 2375849Notes

Reaction equation

HRID 2375849 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O.CCOC(C)=O>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 178526745HCID 178526745, compound

Product 1

HCID 587099233-Nitro-1-(2-phenylethyl)-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-nitro-1H-pyrazole (226 mg, 2.0 mmol) in N,N-dimethylformamide (3 mL) were added potassium carbonate (0.33 g, 2.4 mmol) and 1-bromo-2-phenylethane (0.44 g, 2.4 mmol). The resulting mixture was stirred at rt overnight. TLC showed the reaction was complete. The mixture was diluted with EtOAc (40 mL), then washed with water (2×20 mL), brine (20 mL), and dried over anhydrous sodium sulfate. The crude material was purified by chromatography on silica gel, eluting with Hex:EtOAc=80:20→70:30 to give the title compound as a white solid. NOE experiment confirmed the structure. 1H NMR (CDCl3, 400 MHz): δ=3.22 (t, J=7.1 Hz, 2H), 4.43 (t, J=7.1 Hz, 2H), 6.79 (d, J=2.5 Hz, 1H), 7.06-7.09 (m, 2H), 7.12 (d, J=2.5 Hz, 1H), 7.23-7.32 (m, 3H).

Workup

  1. washwashed with water (2×20 mL), brine (20 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe crude material was purified by chromatography on silica gel
  4. washeluting with Hex

Sources & evidence

ORD record
ord-ba21d19fd9e24ab1b8a7873cb5a17182
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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