Ethanol → Ethyl N-phenylbenzenecarboximidothioate

HRID 2176336Notes

Reaction equation

HRID 2176336 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 this mixed solution was stirred at room temperature for 1 hour. Then, 3.7 mL of iodoethane was added to this mixed solution, and 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 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. After the washing, 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 synthetic scheme of Step 1 is shown by (a-5).

Workup

  1. temperatureheated
  2. stirringstirred at 60° C. for 6 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. additionAfter the washing, 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%)

Sources & evidence

ORD record
ord-85c4f829e8c847ae83269f638e7a2c5d
Source dataset
uspto-grants-2015_06
Patent number
US09065061B2

Reaction notes

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