Benzyl Bromide → HCID 22114954, compound

HRID 1276107Notes

Reaction equation

HRID 1276107 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:11][C:12]1[C:27]([C:28]2[CH2:32][CH2:31][O:30][N:29]=2)=[C:26]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:25]=[CH:24][C:13]=1[C:14]([C:16]1[CH:17]=[N:18][N:19]([CH2:22][CH3:23])[C:20]=1[OH:21])=[O:15]>O1CCOCC1>[CH2:3]([O:21][C:20]1[N:19]([CH2:22][CH3:23])[N:18]=[CH:17][C:16]=1[C:14](=[O:15])[C:13]1[CH:24]=[CH:25][C:26]([S:33]([CH3:36])(=[O:35])=[O:34])=[C:27]([C:28]2[CH2:32][CH2:31][O:30][N:29]=2)[C:12]=1[Cl:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178463115HCID 178463115, compound

Product 1

HCID 22114954HCID 22114954, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.44 g (60 mmol) of sodium hydride and 10.40 g (60 mmol) of benzyl bromide were added a little at a time to a solution of 6.00 g (15 mmol) of 4-[2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-ethyl-5-hydroxy-1H-pyrazole in 300 ml of dry dioxane. The mixture was stirred under reflux for 24 hours, the solvent was removed under reduced pressure and the residue was taken up in dichloromethane and washed three times with water. The organic phase was dried and concentrated and the residue was chromatographed over silica gel (eluent: N-pentane/ethyl acetate). 1.5 g (20% of theory) of 5-benzyloxy-4-[2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-ethyl-1H-pyrazole were obtained (mp.: 70-75° C.).

Workup

  1. temperatureunder reflux for 24 hours
  2. customthe solvent was removed under reduced pressure
  3. washwashed three times with water
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customthe residue was chromatographed over silica gel (eluent: N-pentane/ethyl acetate)

Sources & evidence

ORD record
ord-0acfb76be2bd44cc9870d9a73bb8c7cd
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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