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

HRID 1727747Notes

Reaction equation

HRID 1727747 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-187065c620424503b662ac32da656d70
Source dataset
uspto-grants-2009_02
Patent number
US07495102B2

Reaction notes

Loading…