Sodium Azide → HCID 18549814, compound

HRID 649824Notes

Reaction equation

HRID 649824 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=[N:10]1.[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:18]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=[N:10]1)=[N+:19]=[N-:20]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 18549818HCID 18549818, compound

Product 1

HCID 18549814HCID 18549814, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 1-[2-(bromomethyl)phenyl]pyrazole-5-carboxylate (1.30 g, 4.40 mmol) in 10 mL of N,N-dimethylformamide was added sodium azide (2.86 g, 44.0 mmol). This mixture was stirred at ambient temperature for 48 h and then was diluted with ethyl acetate. The organics were washed with water and brine, dried (MgSO4) and concentrated to afford 0.80 g (71%) of the title compound which was used directly without purification. LRMS (ES+): 280.1 (M+Na)+.

Workup

  1. washThe organics were washed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f9fb5d1b5ddc4df2827ca18bee162b1a
Source dataset
uspto-grants-2001_08
Patent number
US06271237B1

Reaction notes

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