Water → 1-(1-iodo-2-methylpropan-2-yl)-4-nitro-1H-pyrazole

HRID 714832Notes

Reaction equation

CS(O[CH2:6][C:7]([CH3:17])([N:9]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[N:10]1)[CH3:8])(=O)=O.[I-:18].[Na+].O>CN(C)C=O>[I:18][CH2:6][C:7]([N:9]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[N:10]1)([CH3:17])[CH3:8]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of the crude 2-methyl-2-(4-nitro-1H-pyrazol-1-yl)propyl methanesulfonate (18 g) obtained in Step A of Example 115 in N,N-dimethylformamide (150 mL) was added sodium iodide (20 g), and the mixture was stirred overnight at 130° C. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (14 g).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe obtained organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-f3a141bfa52543eab0afb0e03de9ae97
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187453B2

Reaction notes

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