Toluene → HCID 56942880, compound

HRID 335419Notes

Reaction equation

HRID 335419 reaction equation
[CH2:1]([N:8]([C:17](=[O:31])[C:18]([C:20]1[C:25]([CH2:26][CH3:27])=[CH:24][C:23]([CH3:28])=[CH:22][C:21]=1[CH2:29][CH3:30])=O)[N:9]=[C:10]([CH3:16])[CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:1]([N:8]1[C:17](=[O:31])[C:18]([C:20]2[C:25]([CH2:26][CH3:27])=[CH:24][C:23]([CH3:28])=[CH:22][C:21]=2[CH2:29][CH3:30])=[C:11]([S:12]([CH3:15])(=[O:14])=[O:13])[C:10]([CH3:16])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 11430Potassium CarbonateHCID 86689348HCID 86689348, compound

Product 1

HCID 56942880HCID 56942880, compoundYield 20.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 20 ml volume three-necked flask, 1-benzyl-1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-(1-methylsulfonyl-2-propylidene)hydrazine ((4-34)-(7)-39) (340 mg), toluene (3.0 ml), and potassium carbonate (0.18 g) were added at room temperature, then additional toluene (0.5 ml) was added. The resulting mixture was stirred at room temperature for 15 hours, then at the internal temperature of about 50° C. for 18 hours. To the resulting mixture, water was added was extracted with tert-butyl methyl ether. The organic layer was concentrated under reduced pressure, purified by column chromatography (hexane:ethyl acetate=5:1), further recrystallized from ethyl acetate to give 67.5 mg of 2-benzyl-4-(2,6-diethyl-4-methylphenyl)-6-methyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-34)-(7)-39).

Workup

  1. waitat the internal temperature of about 50° C. for 18 hours
  2. extractionwas extracted with tert-butyl methyl ether
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. custompurified by column chromatography (hexane:ethyl acetate=5:1)
  5. customfurther recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-41bc222240a04e0098faf0cf292248fe
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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