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Water → tert-butyl (2-(4-nitro-1H-pyrazol-1-yl)ethyl)carbamate

HRID 714899
Notes
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Reaction equation

HRID 714899 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[C:9]([O:13][C:14](=[O:19])[NH:15][CH2:16][CH2:17]Br)([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[C:9]([O:13][C:14](=[O:19])[NH:15][CH2:16][CH2:17][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1)([CH3:12])([CH3:11])[CH3:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 70984700tert-butyl (2-(4-nitro-1H-pyrazol-1-yl)ethyl)carbamateYield 114.7%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-nitro-1H-pyrazole (5.0 g) in N,N-dimethylformamide (100 mL) were added tert-butyl(2-bromoethyl)carbamate (12 g) and cesium carbonate (19 g), and the mixture was stirred overnight at 40° C. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous sodium 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 (13 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium 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-99bc1ac41863423ea4bb1f28f3e3f300
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