4-Methylbenzyl chloride → N,N-bis(4-Methoxybenzyl)-4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide

HRID 1166283Notes

Reaction equation

HRID 1166283 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1.[C:23](=[O:26])([O-])[O-].[K+].[K+].C[C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1.[C:38]([O:41][CH2:42][CH3:43])(=O)C>CN(C=O)C.O>[CH3:38][O:41][C:42]1[CH:43]=[CH:4][C:3]([CH2:13][N:22]([CH2:34][C:33]2[CH:32]=[CH:31][C:30]([O:26][CH3:23])=[CH:37][CH:36]=2)[S:19]([C:16]2[CH:17]=[CH:18][C:13]([C:3]3[C:4]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)=[N:5][O:6][C:2]=3[CH3:1])=[CH:14][CH:15]=2)(=[O:21])=[O:20])=[CH:2][CH:1]=1

Participants

7

Reactant 4

HCID 77224-Methylbenzyl chlorideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 119607Valdecoxib

Product 1

HCID 12085112N,N-bis(4-Methoxybenzyl)-4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(5-methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide (3.14 g, 0.01 mol) and potassium carbonate (5.53 g, 0.04 mol) in DMF (50 mL) was stirred at room temperature for 5 hours. 4-methylbenzylchloride (3.45 g, 0.022 mol) was then added and the resulting mixture was stirred overnight. Ethyl acetate (50 mL) and sat. water (100 mL) were then added and the layers were separated. The organic layer was washed with NaHCO3 (50 mL), brine, 1 N HCl (25 mL) and water (2×25 mL). Then the organic layer was then dried over MgSO4, filtered and concentrated under vacuum. The resulting product was crystallized from boiling ethanol to afford 5.2 g of the product as a white solid: mp, 133.8-135.2° C.

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. customthe layers were separated
  3. washThe organic layer was washed with NaHCO3 (50 mL), brine, 1 N HCl (25 mL) and water (2×25 mL)
  4. dry with materialThen the organic layer was then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe resulting product was crystallized

Sources & evidence

ORD record
ord-78ce9c48264546b08e52025e4bf9edbf
Source dataset
uspto-grants-2003_09
Patent number
US06613790B2

Reaction notes

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