Diethyl Ether → HCID 67692355, compound

HRID 1683813Notes

Reaction equation

HRID 1683813 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH2:13][C:12](=[O:14])[NH:11][N:10]=1.Br[CH2:16][CH2:17][CH3:18].C(OCC)C>CN(C)C=O.O>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH2:13][C:12](=[O:14])[N:11]([CH2:16][CH2:17][CH3:18])[N:10]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 12523181HCID 12523181, compound

Product 1

HCID 67692355HCID 67692355, compoundYield 111.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.29 g (7.3 mmol) of 60% oily sodium hydride in 10 ml of anhydrous dimethylformamide was added dropwise a solution of 1.2 g (6.2 mmol) of 3-(2-pyridyl)-4, 5-dihydropyrazol-5-one in dimethylformamide (10 ml) at 0° C. After one hour of stirring at room temperature, 0.92 g (7.5 mmol) of 1-bromopropane was added dropwise and stirring was continued for another 18 hours. To the reaction solution was added 50 ml of diethyl ether and 50 ml of water, and vigorously agitated. The resultant solution was separated, and the aqueous layer was extracted twice with 50 ml of ethyl acetate. The organic layer was combined and washed successively with water and saturated brine solution, and dried over anhydrous sodium sulfate. Then the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1 (v/v)) to give 1.4 g of the object compound as a colorless oil (yield 96%).

Workup

  1. stirringstirring
  2. waitwas continued for another 18 hours
  3. stirringvigorously agitated
  4. customThe resultant solution was separated
  5. extractionthe aqueous layer was extracted twice with 50 ml of ethyl acetate
  6. washwashed successively with water and saturated brine solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThen the solvent was evaporated under reduced pressure
  9. customThe obtained crude product
  10. customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1 (v/v))

Sources & evidence

ORD record
ord-6f62388eaa194410818d712724df88b4
Source dataset
uspto-grants-1997_06
Patent number
US05639776

Reaction notes

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