Water → 1-[2-(2,4,6-Triethylphenyl)-2-oxoacetyl]-2-(1,1,1-trifluoro-3-methylsulfanyl-2-propylidene)-1-methylhydrazine

HRID 335423Notes

Reaction equation

HRID 335423 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](=[O:19])[C:14]([N:16]([CH3:18])[NH2:17])=[O:15])[CH3:2].[F:20][C:21]([F:28])([F:27])[C:22](=O)[CH2:23][S:24][CH3:25].O>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[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](=[O:19])[C:14]([N:16]([CH3:18])[N:17]=[C:22]([CH2:23][S:24][CH3:25])[C:21]([F:28])([F:27])[F:20])=[O:15])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 140647491,1,1-Trifluoro-3-methylsulfanyl-2-propanoneHCID 666955611-[2-(2,4,6-Triethylphenyl)-2-oxoacetyl]-1-methylhydrazine

Product 1

HCID 764690261-[2-(2,4,6-Triethylphenyl)-2-oxoacetyl]-2-(1,1,1-trifluoro-3-methylsulfanyl-2-propylidene)-1-methylhydrazineYield 50%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

To a 100 ml volume three-necked flask, 1-[2-(2,4,6-triethylphenyl)-2-oxoacetyl]-1-methylhydrazine ((12-2)-(11)-40) (3.01 g) was added, and to the mixture was added dropwise a solution of 1,1,1-trifluoro-3-methylsulfanyl-2-propanone (7-0-2) (2.10 g) in toluene (27 g), followed by the addition of para-toluenesulfonic acid monohydrate (0.030 g). The resulting mixture was stirred under reflux for 40 minutes. Then, the reaction mixture was cooled to room temperature, poured into water (30 ml), and extracted with ethyl acetate (50 ml) 3 times. The resulting organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and subjected to silica gel column chromatography (chloroform) to give 2.31 g of 1-[2-(2,4,6-triethylphenyl)-2-oxoacetyl]-2-(1,1,1-trifluoro-3-methylsulfanyl-2-propylidene)-1-methylhydrazine ((4-46)-(1)-40).

Workup

  1. temperatureunder reflux for 40 minutes
  2. extractionextracted with ethyl acetate (50 ml) 3 times
  3. dry with materialThe resulting organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-13506a7d51834b1c9533f04391583bfc
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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