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

HRID 714833Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 1-(1-iodo-2-methylpropan-2-yl)-4-nitro-1H-pyrazole (14 g) obtained in Step B of Example 115 in N,N-dimethylformamide (100 mL) was added sodium azide (4.8 g), and the mixture was stirred overnight at 140° 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 (10 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-415068073e4e49df87c83d8f5da6e046
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187453B2

Reaction notes

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