Sodium → 3-Cyclopropyl-5-nitro-1H-pyrazole

HRID 324570Notes

Reaction equation

HRID 324570 reaction equation
[OH2:1].[Na].[CH:3]1([C:6]2[CH:10]=[C:9]([NH2:11])[NH:8][N:7]=2)[CH2:5][CH2:4]1.[Na].[OH:13]OS([O-])=O.[K+]>O.CC(C)=O>[CH:3]1([C:6]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:1])[NH:8][N:7]=2)[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 5360545SodiumHCID 23707502Potassium hydroxy sulfiteHCID 71353970Sodium monohydrateHCID 178507266HCID 178507266, compound

Product 1

HCID 1354511303-Cyclopropyl-5-nitro-1H-pyrazoleYield 52%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent3×

Procedure

To a solution of 2.7 g of sodium hydrate in 454 ml of water 7.1 g (0.058 mol) of 3-cyclopropyl-5-amino-1H-pyrazole and 46.5 g of sodium hydrogenocarbonate were added at 0° C. After 10 minutes a solution of 337 ml of acetone in 221 ml of water and a solution of 130 g (0.21 mol) of oxone in 580 ml of water were contemporaneously dropped under vigorous stirring. After 4 hours at the same temperature the reaction is quenched with a saturated solution of sodium sulfite and extracted with ethylacetate. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness to give 4.6 g (52% yield) of the title compound.

Workup

  1. customAfter 4 hours at the same temperature the reaction is quenched with a saturated solution of sodium sulfite
  2. extractionextracted with ethylacetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-9160f4a259fd48c781dce9e9a126eecf
Source dataset
uspto-grants-2001_04
Patent number
US06218418B1

Reaction notes

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