Hydrochloric Acid → 5-[(2,6-diethyl-4-methylphenyl)carbonyl]-3-(4-fluorophenyl)-1-methyl-4-methylsulfonyl-1H-pyrazole

HRID 579252Notes

Reaction equation

HRID 579252 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:31])[C:13]([N:15]([CH3:30])[N:16]=[C:17]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH2:18][S:19]([CH3:22])(=[O:21])=[O:20])=[O:14])[CH3:2].CO.O.[OH-].[Li+].Cl>O>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:14])[N:15]([CH3:30])[N:16]=[C:17]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:18]=1[S:19]([CH3:22])(=[O:21])=[O:20])[CH3:2].[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]([C:13]1[N:15]([CH3:30])[N:16]=[C:17]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:18]=1[S:19]([CH3:22])(=[O:21])=[O:20])=[O:31])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 866893541-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-2-[1-(4-fluorophenyl)-2-methylsulfonylethylidene]-1-methylhydrazine

Product 2

HCID 666930525-[(2,6-diethyl-4-methylphenyl)carbonyl]-3-(4-fluorophenyl)-1-methyl-4-methylsulfonyl-1H-pyrazoleHCID 866893554-(2,6-Diethyl-4-methylphenyl)-6-(4-fluorophenyl)-2-methyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

To a 10 ml volume two-necked flask, 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-[1-(4-fluorophenyl)-2-methylsulfonylethylidene]-1-methyl-2-oxoacetohydrazide ((4-64)-(1)-39) (0.66 g) and methanol (2.5 ml) were added under a nitrogen atmosphere. To the mixture, lithium hydroxide monohydrate (62 mg) was added under cooling on −5° C. bath, and stirred under ice-cooling for 4 hours. After cold dilute hydrochloric acid was added under ice-cooling, the mixture was added to cold water, and extracted with ethyl acetate 3 times. The organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography (hexane: ethyl acetate=3:1) to give 0.31 g of 4-(2,6-diethyl-4-methylphenyl)-6-(4-fluorophenyl)-2-methyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-64)-(1)-39) and 0.12 mg of 5-[(2,6-diethyl-4-methylphenyl)carbonyl]-3-(4-fluorophenyl)-1-methyl-4-methylsulfonyl-1H-pyrazole (22-b).

Workup

  1. temperaturecooling for 4 hours
  2. temperaturecooling
  3. extractionextracted with ethyl acetate 3 times
  4. washThe organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d0af3bf972f34fb49aac63bec86b9367
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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