Sodium hydride → 3-(Pyrazol-1-yloxy)-propylphthalimide

HRID 232021Notes

Reaction equation

HRID 232021 reaction equation
[OH:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.[H-].[Na+].Br[CH2:10][CH2:11][CH2:12][C:13]1[CH:23]=[CH:22][CH:21]=[C:15]2[C:16]([NH:18][C:19](=[O:20])[C:14]=12)=[O:17]>C1(C)C(C)=CC=CC=1>[N:2]1([O:1][CH2:10][CH2:11][CH2:12][C:13]2[CH:23]=[CH:22][CH:21]=[C:15]3[C:16]([NH:18][C:19](=[O:20])[C:14]=23)=[O:17])[CH:6]=[CH:5][CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 30167331-hydroxy-1H-pyrazoleHCID 21958088Bromopropylphthalimide

Product 1

HCID 200307663-(Pyrazol-1-yloxy)-propylphthalimideYield 101.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

26 g of 1-hydroxypyrazole are added to a suspension of 10 g of sodium hydride (80 percent strength in oil) in 500 ml of xylene. The mixture is stirred for 1 hour, after which 84 g of 3-bromopropylphthalimide are added and the mixture is refluxed for 2 hours. After cooling, the mixture is filtered, the filtrate is evaporated down, the crystalline residue is suspended in diethyl ether and the product is filtered off under suction. 85 g of the title compound of melting point 116°-118° C. are obtained.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. customthe filtrate is evaporated down
  5. filtrationthe product is filtered off under suction

Sources & evidence

ORD record
ord-6b08d5eaf34d4792b1c35cff93a5f683
Source dataset
uspto-grants-1989_07
Patent number
US04851410

Reaction notes

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