Hydrochloric Acid → HCID 68095685, compound

HRID 335425Notes

Reaction equation

HRID 335425 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:27])[N:15]([CH3:26])[N:16]=[C:17]([C:22]([F:25])([F:24])[F:23])[C:18]=1S(C)=O)[CH3:2].CN1CCCC1=[O:34].[OH-].[Na+].Cl>O>[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:27])[N:15]([CH3:26])[N:16]=[C:17]([C:22]([F:25])([F:24])[F:23])[C:18]=1[OH:34])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 86689349HCID 86689349, compound

Product 1

HCID 68095685HCID 68095685, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

To a 50 ml volume three-necked flask, 4-(2,4,6-triethylphenyl)-2-methyl-5-methylsulfinyl-6-trifluoromethyl-2,3-dihydro-3-pyridazinone ((2-49)-(1)-40) (0.692 g), N-methylpyrrolidone (6.40 g), water (3.11 g), and sodium hydroxide (0.626 g) were added at room temperature. The resulting mixture was stirred at 50° C. for 4 hours. The reaction mixture was cooled to room temperature, added 12N hydrochloric acid (3 ml) and water (15 ml), and extracted with ethyl acetate (30 ml) 3 times. The combined organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and subjected to silica gel column chromatography (hexane:ethyl acetate=8:1 to hexane:ethyl acetate=5:1 to hexane:ethyl acetate=3:1). Then, the resulting fraction was concentrated under reduced pressure, recrystallized from hexane to give 0.331 g of 4-(2,4,6-triethylphenyl)-5-hydroxy-2-methyl-6-trifluoromethyl-2,3-dihydro-3-pyridazinone ((1-16)-(1)-40) on the filter paper.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (30 ml) 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. concentrationThen, the resulting fraction was concentrated under reduced pressure
  6. customrecrystallized from hexane

Sources & evidence

ORD record
ord-ea36536d30804c38a2ca967ab435ed71
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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