Potassium Carbonate → 1-(4-Methoxybenzyl)-4-nitro-1H-pyrazole
Reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1>CN(C)C=O>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]2)=[CH:18][CH:19]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
4-Nitro-1H-pyrazole (1 g, 8.84 mmol) was dissolved in dimethylformamide (40 ml). Potassium carbonate (1.2 g, 8.68 mmol) and 1-(chloromethyl)-4-methoxybenzene (1.2 g, 8.96 mmol) were added and the mixture was heated with stirring at 80° C. for 3 h. Once at room temperature, the reaction mixture was poured onto water and extracted with ethyl acetate (x3). The organic phase was washed with water and brine, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure to yield 2.27 g of the final compound as an oil. The product was used in the next synthetic step without further purification.
Workup
- temperaturethe mixture was heated
- additionOnce at room temperature, the reaction mixture was poured onto water
- extractionextracted with ethyl acetate (x3)
- washThe organic phase was washed with water and brine
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- customthe solvent evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-d49d1065590c43929e8710a8abd307f2
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340547B2
Reaction notes
Loading…