3-Chlorobenzoic Acid → HCID 56943037, compound

HRID 579235Notes

Reaction equation

HRID 579235 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]1[C:13](=[O:25])[N:14]([CH3:24])[N:15]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:17]=1[S:18][CH3:19])[CH3:2].C(=O)([O-])[OH:27].[Na+].ClC1C=C(C=CC=1)C(O)=O.S([O-])([O-])=O.[Na+].[Na+]>O.C(Cl)(Cl)Cl>[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:25])[N:14]([CH3:24])[N:15]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:17]=1[S:18]([CH3:19])=[O:27])[CH3:2]

Participants

7

Reactant 4

HCID 4473-Chlorobenzoic AcidHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 56943036HCID 56943036, compound

Product 1

HCID 56943037HCID 56943037, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a 50 ml volume three-necked flask, 4-(2,6-diethyl-4-methylphenyl)-2-methyl-5-methylsulfanyl-6-trifluoromethyl-2,3-dihydro-3-pyridazinone ((2-46)-(1)-39) (0.51 g) and chloroform (12.5 ml) were added at room temperature. Sodium hydrogen carbonate (0.46 g) and meta-chlorobenzoic acid (0.48 g) was added and the resulting mixture was stirred at room temperature for 3 hours. Then, the reaction mixture was poured into water (20 ml), added sodium sulfite (0.3 g), and extracted with t-butyl methyl ether (40 ml) 2 times. Then, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and subjected to silica gel column chromatography (hexane: ethyl acetate=3:1 to hexane: ethyl acetate=1:1) to give 0.461 g of 4-(2,6-diethyl-4-methylphenyl)-2-methyl-5-methylsulfinyl-6-trifluoromethyl-2,3-dihydro-3-pyridazinone ((2-49)-(1)-39).

Workup

  1. extractionextracted with t-butyl methyl ether (40 ml) 2 times
  2. washThen, the organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fcfc6885cffc4bb0be9694a9916ad1d1
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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