Ethanol → HCID 13115188, compound

HRID 2176332Notes

Reaction equation

HRID 2176332 reaction equation
[O-][CH2:2][CH3:3].[Na+].[C:5]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[S:7])[CH3:6].C(O)C.ICC>ClCCl>[CH2:2]([S:7][C:5](=[N:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6])[CH3:3]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 6340IodoethaneHCID 820777N-PhenylethanethioamideHCID 2723922Sodium ethoxide

Product 1

HCID 13115188HCID 13115188, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Next, 4.5 g of sodium ethoxide, 9.8 g of thioacetanilide, and 50 mL of ethanol were put in a 100 mL three-neck flask, and stirred at room temperature for 1 hour. Then, 5.3 mL of iodoethane was added to this mixture, and heated and stirred at 60° C. for 5 hours to be reacted. After the reaction, ethanol was distilled off under a reduced pressure to give a brown oily substance. This oily substance was dissolved in dichloromethane, and washed with water and then a saturated aqueous solution of sodium hydrogen carbonate. Anhydrous magnesium sulfate was added to the resulting organic layer for drying. After the drying, the solution was subjected to gravity filtration. The resulting filtrate was concentrated, so that N-[1-(ethylsulfanyl)ethylidene]aniline was prepared (a brown solid, yield: 73%). The synthetic scheme of Step 2 is shown by (b-2).

Workup

  1. temperatureheated
  2. stirringstirred at 60° C. for 5 hours
  3. customto be reacted
  4. distillationwas distilled off under a reduced pressure
  5. customto give a brown oily substance
  6. washwashed with water
  7. additionAnhydrous magnesium sulfate was added to the resulting organic layer
  8. customfor drying
  9. filtrationAfter the drying, the solution was subjected to gravity filtration
  10. concentrationThe resulting filtrate was concentrated, so that N-[1-(ethylsulfanyl)ethylidene]aniline
  11. customwas prepared (a brown solid, yield: 73%)

Sources & evidence

ORD record
ord-33946d52a35040a6834d7d64260c40c6
Source dataset
uspto-grants-2015_06
Patent number
US09065061B2

Reaction notes

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