Chloride → 4-iodo-1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazole

HRID 1843642

Reaction equation

[I:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=2)=[N:4][NH:5][CH:6]=1.[C:16](=[O:19])([O-])[O-].[Cs+].[Cs+].[Cl-].O>CN(C)C=O>[I:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=2)=[N:4][N:5]([CH2:3][C:7]2[CH:12]=[CH:11][C:10]([O:19][CH3:16])=[CH:9][CH:8]=2)[CH:6]=1

Participants

Conditions

Temperature: 70 °C

Procedure

2 g (6.3 mmol) of 4-iodo-3-(3-nitrophenyl)-1H-pyrazole were dissolved in 20 ml of dry dimethylformamide and 2.46 g (7.5 mmol) of cesium carbonate and 0.85 ml (6.3 mmol) of p-methoxybemzyl chloride were added successively. The reaction mixture was heated at 70° C. under stirring for 5 hours. Water was then added and the product extracted with dichloromethane. The organic phase was dried over sodium sulphate and the solvent evaporated under reduced pressure. 2.4 g (86%) of the title compound crystallized from a mixture diethylether-diisopropylether.

Workup

extractionthe product extracted with dichloromethane
dry with materialThe organic phase was dried over sodium sulphate
customthe solvent evaporated under reduced pressure
custom2.4 g (86%) of the title compound crystallized from a mixture diethylether-diisopropylether

Sources & evidence

ORD record: ord-5699b1c5a89f4a2f8cd2327ca4ec1a76
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946250B2

Linked notes

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