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

HRID 714833
Notes
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Reaction equation

HRID 714833 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 1178402261-(1-iodo-2-methylpropan-2-yl)-4-nitro-1H-pyrazole

Product 1

HCID 1178402371-(1-azido-2-methylpropan-2-yl)-4-nitro-1H-pyrazoleYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes