Hydrochloric Acid → HCID 66695563, compound

HRID 335422Notes

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:26])[N:14]([CH3:25])[N:15]=[C:16]([C:21]([F:24])([F:23])[F:22])[C:17]=1S(C)=O)[CH3:2].CN1CCCC1=[O:33].[OH-].[Na+].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:26])[N:14]([CH3:25])[N:15]=[C:16]([C:21]([F:24])([F:23])[F:22])[C:17]=1[OH:33])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a 30 ml volume three-necked flask, 4-(2,6-diethyl-4-methylphenyl)-2-methyl-5-methylsulfinyl-6-trifluoromethyl-2,3-dihydro-3-pyridazinone ((2-49)-(1)-39) (0.375 g), N-methylpyrrolidone (3.49 g), water (1.75 g), and sodium hydroxide (0.34 g) were added at room temperature. The resulting mixture was stirred at 50° C. for 4 hours. Then, the resulting mixture was cooled to room temperature, added 12N hydrochloric acid (1.5 ml) and water (15 ml), and extracted with ethyl acetate (30 ml). The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and subjected to silica gel column chromatography (hexane:ethyl acetate=7:1 to hexane:ethyl acetate=5:1 to hexane:ethyl acetate=3:1) to give 0.147 g of 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2-methyl-6-trifluoromethyl-2,3-dihydro-3-pyridazinone ((1-16)-(1)-39).

Workup

temperatureThen, the resulting mixture was cooled to room temperature
extractionextracted with ethyl acetate (30 ml)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ed8e3992424346b8a3b968139a4ff3c6
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884010B2

Reaction notes

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