Toluene → HCID 67543919, compound

HRID 2061010Notes

Reaction equation

HRID 2061010 reaction equation
[CH2:1]([C:3](=[CH:13][S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O)[CH3:2].S(Cl)(Cl)=O.C1(C)C=CC=CC=1.[Na].[C:33]1([SH:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C>[CH2:1]([C:3](=[CH:13][S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:4]([S:39][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[N:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]

Participants

7

Reactant 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 66586497Sodium benzenethiolHCID 67543373HCID 67543373, compound

Product 1

HCID 67543919HCID 67543919, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.68 g (13 mmol) of 2-ethyl-N-phenyl-3-(phenylthio)-2-propenamide, 1.9 ml (26 mmol) of thionyl chloride, 10 mg of DMF, and 20 ml of toluene was refluxed for 1 hour. After concentration of the mixture under vacuum, the residue was dissolved in 35 ml of DMF and then 2.0 g (15.1 mmol) of a benzenethiol sodium salt was added portionwise under ice cooling and stirred at room temperature for 1 hour. After dilution with tert-butyl methyl ether, the mixture was washed sequentially with water (three times) and saturated NaCl solution, dried over anhydrous MgSO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1) to obtain 2.03 g of phenyl 2-ethyl-N-phenyl-3-(phenylthio)-2-propenimidothioate (hereinafter referred to as the present compound 14).

Workup

  1. temperaturewas refluxed for 1 hour
  2. washAfter dilution with tert-butyl methyl ether, the mixture was washed sequentially with water (three times) and saturated NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-2b0f0199a9404202a425953c05d23e2a
Source dataset
uspto-grants-2012_10
Patent number
US08278473B2

Reaction notes

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