1-Bromopropane → 3,5-dibromo-1-propyl-4-nitro-1H-pyrazole
Reaction equation
[Br:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5]([Br:10])[NH:4][N:3]=1.[H-].[Na+].Br[CH2:14][CH2:15][CH3:16]>CN(C=O)C>[CH2:14]([N:3]1[C:2]([Br:1])=[C:6]([N+:7]([O-:9])=[O:8])[C:5]([Br:10])=[N:4]1)[CH2:15][CH3:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
A mixture of 3,5-dibromo-4-nitropyrazole (2) (25 g, 92 mmol) in DMF (120 ml) was added over 45 minutes to a suspension of NaH (4.0 g, 10 mmol; 60% dispersion in oil, prewashed with hexane) in DMF (200 ml) with stirring and under an inert atmosphere. After stirring for 30 minutes, a solution of 1-bromopropane (13.6 g, 111 mmol) in DMF (40 ml) was added over 10 minutes. The reaction mixture was heated at 50-60° C. for 3 hours (monitored by TLC) and the DMF was then evaporated off under reduced pressure. A mixture of DCM/water (300 ml, 1/5) was added and the organic phase was then extracted with water (2×50 ml). The organic phase was dried over Na2SO4 and the solvent was evaporated off under reduced pressure. The crude reaction product was obtained as a black oil (19.4 g, 70%), which was used without further purification in the amination step.
Workup
- stirringAfter stirring for 30 minutes
- customthe DMF was then evaporated off under reduced pressure
- additionA mixture of DCM/water (300 ml, 1/5)
- additionwas added
- extractionthe organic phase was then extracted with water (2×50 ml)
- dry with materialThe organic phase was dried over Na2SO4
- customthe solvent was evaporated off under reduced pressure
- customThe crude reaction product
Sources & evidence
- ORD record
- ord-ab7550863d0942ffa0f13674e303097d
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07285136B2
Reaction notes
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