Acetyl chloride → HCID 21183161, compound

HRID 1386894Notes

Reaction equation

HRID 1386894 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]([N:9]1[C:13]([OH:14])=[C:12]([C:15](=[O:35])[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:18]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:17]=2[CH3:34])[CH:11]=[N:10]1)([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl>[CH3:8][C:6]([N:9]1[C:13]([O:14][C:1](=[O:3])[CH3:2])=[C:12]([C:15](=[O:35])[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:18]([C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)[C:17]=2[CH3:34])[CH:11]=[N:10]1)([CH3:5])[CH3:7]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178488832HCID 178488832, compound

Product 1

HCID 21183161HCID 21183161, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 0.25 mL of acetyl chloride in 3 mL of dry dichloromethane was added slowly under nitrogen at 0° C. with stirring to a solution of 1.5 g (3.4 mmol) of 1-(1,1-dimethylethyl)-5-hydroxy-4-(2-methyl-4-methylsulfonyl-3-(4-methoxyphenyl)benzoyl)pyrazole and 0.52 mL of triethylamine in about 20 mL of dry dichloromethane. The mixture was allowed to warm to ambient temperature and stir for 2 hours and was then diluted with dichloromethane. The resulting solution was extracted with saturated aqueous sodium bicarbonate solution and with water, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure. The residual yellow oil was chromatographed on silica gel eluting with a 50:50 mixture of ethyl acetate and hexane. The product fractions were combined and concentrated by evaporation under reduced pressure to obtain 1.03 g (62 percent of theory) of the title compound as a white powder melting at 160-163° C.

Workup

  1. extractionThe resulting solution was extracted with saturated aqueous sodium bicarbonate solution and with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residual yellow oil was chromatographed on silica gel eluting with a 50:50 mixture of ethyl acetate and hexane
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-5ce0e0d956284b2bb497f2e9a160572f
Source dataset
uspto-grants-2001_07
Patent number
US06265606B1

Reaction notes

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