Ethanol → Ethyl N-phenylbenzenecarboximidothioate

HRID 1468586Notes

Reaction equation

HRID 1468586 reaction equation
[O-][CH2:2][CH3:3].[Na+].[C:5]1([NH:11][C:12](=[S:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(O)C.ICC>ClCCl>[CH2:2]([S:19][C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N:11][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH3:3]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 6340IodoethaneHCID 668263Benzenecarbothioamide, N-phenyl-HCID 2723922Sodium ethoxide

Product 1

HCID 13377974Ethyl N-phenylbenzenecarboximidothioate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

First, 3.2 g of sodium ethoxide, 10 g of N-phenylthiobenzamide, and 60 mL of ethanol were put in a 300 mL three-neck flask, and stirred at room temperature for 1 hour. Then, 3.7 mL of iodoethane was added to this mixture, and the mixture was heated and stirred at 60° C. for 6 hours to be reacted. After the reaction, ethanol was distilled off under a reduced pressure to give an oily substance. This oily substance was dissolved in dichloromethane, and washed with water and then a saturated aqueous solution of sodium hydrogen carbonate. Then, anhydrous magnesium sulfate was added to the resulting organic layer for drying. The resulting mixture was subjected to gravity filtration, and the filtrate was concentrated, so that N-[(ethylsulfanyl)phenylmethylidene]aniline was prepared (a brown oily substance, crude yield: 110%). The synthesis scheme of Step 1 is shown by (a-1).

Workup

  1. temperaturethe mixture was heated
  2. stirringstirred at 60° C. for 6 hours
  3. customto be reacted
  4. distillationwas distilled off under a reduced pressure
  5. customto give an oily substance
  6. washwashed with water
  7. additionThen, anhydrous magnesium sulfate was added to the resulting organic layer
  8. customfor drying
  9. filtrationThe resulting mixture was subjected to gravity filtration
  10. concentrationthe filtrate was concentrated, so that N-[(ethylsulfanyl)phenylmethylidene]aniline
  11. customwas prepared (a brown oily substance, crude yield: 110%)
  12. customThe synthesis scheme of Step 1

Sources & evidence

ORD record
ord-8fa8d0ea429347b3b77b6350b4ab212f
Source dataset
uspto-grants-2015_04
Patent number
US09005773B2

Reaction notes

Loading…