3-Chlorobenzoic Acid → HCID 86689349, compound

HRID 335424Notes

Reaction equation

HRID 335424 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH3:10])[CH:6]=[C:5]([CH2:11][CH3:12])[C:4]=1[C:13]1[C:14](=[O:26])[N:15]([CH3:25])[N:16]=[C:17]([C:21]([F:24])([F:23])[F:22])[C:18]=1[S:19][CH3:20])[CH3:2].C(=O)([O-])[OH:28].[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]([CH2:9][CH3:10])[CH:6]=[C:5]([CH2:11][CH3:12])[C:4]=1[C:13]1[C:14](=[O:26])[N:15]([CH3:25])[N:16]=[C:17]([C:21]([F:24])([F:23])[F:22])[C:18]=1[S:19]([CH3:20])=[O:28])[CH3:2]

Participants

7

Reactant 4

HCID 4473-Chlorobenzoic AcidHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 66695558HCID 66695558, compound

Product 1

HCID 86689349HCID 86689349, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a 100 ml volume four-necked flask, 4-(2,4,6-triethylphenyl)-2-methyl-5-methylsulfanyl-6-trifluoromethyl-2,3-dihydro-3-pyridazinone ((2-46)-(1)-40) (0.683 g) and chloroform (24 ml) were added at room temperature, and stirred. Sodium hydrogen carbonate (0.597 g) and meta-chlorobenzoic acid (0.615 g) was added and the resulting mixture was stirred at room temperature for 4 hours. Then, the reaction mixture was poured into water (30 ml), added sodium sulfite (0.4 g), and extracted with t-butyl methyl ether (30 ml) 4 times. The combined 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=5:1 to hexane:ethyl acetate=1:1) to give 0.692 g of 4-(2,4,6-triethylphenyl)-2-methyl-5-methylsulfinyl-6-trifluoromethyl-2,3-dihydro-3-pyridazinone ((2-49)-(1)-40).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 4 hours
  2. extractionextracted with t-butyl methyl ether (30 ml) 4 times
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f5bafae5ee894544a606cccc2507cc32
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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