Iodoethane → 4-Bromo-1-ethyl-3-(4-nitrophenyl)-1H-pyrazole

HRID 1821228Notes

Reaction equation

HRID 1821228 reaction equation
[Br:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)=[N:4][NH:5][CH:6]=1.[H-].[Na+].I[CH2:19][CH3:20]>CN(C)C=O>[Br:1][C:2]1[C:3]([C:7]2[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=2)=[N:4][N:5]([CH2:19][CH3:20])[CH:6]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178526566HCID 178526566, compound

Product 1

HCID 689971424-Bromo-1-ethyl-3-(4-nitrophenyl)-1H-pyrazoleYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0° C. solution of 4-bromo-3-(4-nitrophenyl)-1H-pyrazole (485 mmol) in N,N-dimethylformamide (1000 mL) was slowly treated with sodium hydride (485 mmol) and then iodoethane (582 mmol). The reaction mixture was stirred for 30 minutes at room temperature and then poured into ice-water (1000 mL). Product precipitated out of solution and was collected by filtration, washed with water (4×500 mL) and dried to provide the title product as a light brown powder (94%). ESMS [M+H]+: 297.2

Workup

  1. customProduct precipitated out of solution
  2. filtrationwas collected by filtration
  3. washwashed with water (4×500 mL)
  4. customdried

Sources & evidence

ORD record
ord-eab5ea66b8054deb8897cb27d14e90f7
Source dataset
uspto-grants-2009_10
Patent number
US07605266B2

Reaction notes

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