Benzoyl chloride → HCID 67815312, compound

HRID 244944Notes

Reaction equation

HRID 244944 reaction equation
[Br:1][CH:2]1[C:6](=[O:7])[N:5]([C:8]([CH3:17])([CH3:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:4]=[C:3]1[CH:18]([CH3:20])[CH3:19].C(N(CC)CC)C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[C:28]([O:7][C:6]1[N:5]([C:8]([CH3:16])([CH3:17])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:4]=[C:3]([CH:18]([CH3:20])[CH3:19])[C:2]=1[Br:1])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67811749HCID 67811749, compound

Product 1

HCID 67815312HCID 67815312, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromo-3-isopropyl-1-(2-methyl-1-phenylpropan-2-yl)-1H-pyrazol-5(4H)-one (3.00 g, 8.90 mmol) was dissolved in 39 mL of tetrahydrofuran and cooled with ice to 0° C., and after dropwise addition of 1.80 g (17.8 mmol) of triethylamine and 1.38 g (9.82 mmol) of benzoyl chloride, stirred at room temperature for 3 hours under a nitrogen atmosphere. The reaction was quenched with distilled water, and the reaction solution was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (silica gel 12 g, ethyl acetate:hexane=1:20) to give 3.34 g of the desired product as a yellow oil.

Workup

  1. customThe reaction was quenched with distilled water
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (silica gel 12 g, ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-3787d6a30bbf453fa0a6ba8df44c6adc
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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