Benzyl Bromide → HCID 15477455, compound

HRID 1857321Notes

Reaction equation

HRID 1857321 reaction equation
[O:1]1[CH2:5][CH2:4][C:3]([C:6]2[C:7]([CH3:25])=[C:8]([CH:18]=[CH:19][C:20]=2[S:21]([CH3:24])(=[O:23])=[O:22])[C:9]([C:11]2[CH:12]=[N:13][N:14]([CH3:17])[C:15]=2[OH:16])=[O:10])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C>[CH2:32]([O:16][C:15]1[N:14]([CH3:17])[N:13]=[CH:12][C:11]=1[C:9](=[O:10])[C:8]1[CH:18]=[CH:19][C:20]([S:21]([CH3:24])(=[O:23])=[O:22])=[C:6]([C:3]2[CH2:4][CH2:5][O:1][N:2]=2)[C:7]=1[CH3:25])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178428868HCID 178428868, compound

Product 1

HCID 15477455HCID 15477455, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.45 g of 4-[3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl]-5-hydroxy-1-methylpyrazole was dissolved in 15 ml of DMF, and 0.26 g of potassium carbonate, then 0.25 g of benzyl 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 0.42 g of the title compound as white crystals. m.p. 151.5~153° 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-8c2bed5b8a474519840252f6d004d614
Source dataset
uspto-grants-2000_11
Patent number
US06147031

Reaction notes

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