Phenacyl bromide → 4-[3-(4,5-Dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl]-1-ethyl-5-phenacyloxypyrazole

HRID 1857322Notes

Reaction equation

HRID 1857322 reaction equation
[O:1]1[CH2:5][CH2:4][C:3]([C:6]2[C:7]([CH3:26])=[C:8]([CH:19]=[CH:20][C:21]=2[S:22]([CH3:25])(=[O:24])=[O:23])[C:9]([C:11]2[CH:12]=[N:13][N:14]([CH2:17][CH3:18])[C:15]=2[OH:16])=[O:10])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:35]>CN(C=O)C>[O:1]1[CH2:5][CH2:4][C:3]([C:6]2[C:7]([CH3:26])=[C:8]([CH:19]=[CH:20][C:21]=2[S:22]([CH3:25])(=[O:24])=[O:23])[C:9]([C:11]2[CH:12]=[N:13][N:14]([CH2:17][CH3:18])[C:15]=2[O:16][CH2:33][C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:35])=[O:10])=[N:2]1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 178463114HCID 178463114, compound

Product 1

HCID 154774574-[3-(4,5-Dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl]-1-ethyl-5-phenacyloxypyrazoleYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.20 g of 4-[3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl]-1-ethyl-5-hydroxypyrazole was dissolved in 10 ml of DMF, and 0.11 g of potassium carbonate, then 0.13 g of phenacyl bromide were added. The resulting solution was stirred at room temperature overnight. The reaction solution was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with water, then with a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure. Methanol was added to the residue. The obtained crystals were separated by filtration to give 0.17 g of the title compound as white crystals. m.p. 177~179° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwith a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled out under reduced pressure
  5. additionMethanol was added to the residue
  6. customThe obtained crystals were separated by filtration

Sources & evidence

ORD record
ord-abb9c3034bb7408e91264ea05b3bd8b6
Source dataset
uspto-grants-2000_11
Patent number
US06147031

Reaction notes

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