Benzyl Chloride → HCID 21183190, compound

HRID 1386895Notes

Reaction equation

HRID 1386895 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([N:13]1[C:17]([OH:18])=[C:16]([C:19](=[O:39])[C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[C:22]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[C:21]=2[CH3:38])[CH:15]=[N:14]1)([CH3:12])[CH3:11].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>CN(C)C=O>[CH3:12][C:10]([N:13]1[C:17]([O:18][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:16]([C:19](=[O:39])[C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[C:22]([C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)[C:21]=2[CH3:38])[CH:15]=[N:14]1)([CH3:9])[CH3:11]

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 178488832HCID 178488832, compound

Product 1

HCID 21183190HCID 21183190, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl chloride (1.1 mL) was added with stirring under nitrogen to a mixture of 2.0 g (4.5 mmol) of 1-(1,1-dimethylethyl)-5-hydroxy-4-(2-methyl-4-methylsulfonyl-3-(4-methoxyphenyl)benzoyl)pyrazole and 1.3 g of sodium carbonate in about 20 mL of dry N,N-dimethylformamide and the resulting mixture was allowed to stir overnight. Ethyl acetate was then added and the resulting mixture was washed with water several times, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure. The residual orange oil was chromatographed on silica eluting with an 80:20 mixture and then a 60:40 mixture of hexane and ethyl acetate. The product fractions were combined and concentrated by evaporation under reduced pressure and dried to obtain 1.73 g (72 percent of theory) of the title compound as a yellow glass.

Workup

  1. washthe resulting mixture was washed with water several times
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residual orange oil was chromatographed on silica eluting with an 80:20 mixture
  6. additiona 60:40 mixture of hexane and ethyl acetate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customdried

Sources & evidence

ORD record
ord-3ffd47347ed243ac83d4345591511c1b
Source dataset
uspto-grants-2001_07
Patent number
US06265606B1

Reaction notes

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