Sodium Azide → 3,5-Dimethyl 1-(3-azidopropyl)-1H-pyrazole-3,5-dicarboxylate

HRID 399435Notes

Reaction equation

HRID 399435 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]([C:14]([O:16][CH3:17])=[O:15])=[N:6]1.[N-:18]=[N+:19]=[N-:20].[Na+]>CS(C)=O.O>[N:18]([CH2:2][CH2:3][CH2:4][N:5]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]([C:14]([O:16][CH3:17])=[O:15])=[N:6]1)=[N+:19]=[N-:20]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 18967494HCID 18967494, compound

Product 1

HCID 107542893,5-Dimethyl 1-(3-azidopropyl)-1H-pyrazole-3,5-dicarboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 5-1 (1.0 g, 3.45 mmol) in 10 ml DMSO was treated with NaN3 (0.883 g, 13.8 mmol) and mixture stirred at 25° C. for 5 h. Next, the reaction mixture was diluted with 100 ml of H2O and then extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with water (2×100 ml) and brine (1×100 ml), dried over Na2SO4 and evaporated to give 5-2 as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washThe combined organic extracts were washed with water (2×100 ml) and brine (1×100 ml)
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-b4b3941c59ac4acea0d0be7cf7fa92c5
Source dataset
uspto-grants-1998_10
Patent number
US05821241

Reaction notes

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