Lawesson's reagent → N-[2-(3-cyanophenoxy)ethyl]-4-cyanobenzthioamide

HRID 747659Notes

Reaction equation

HRID 747659 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[O:6][CH2:7][CH2:8][NH:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)#[N:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:32]2)=CC=1>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[O:6][CH2:7][CH2:8][NH:9][C:10](=[S:32])[C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)#[N:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 11066232N-[2-(3-cyanophenoxy)ethyl]-4-cyanobenzamide

Product 1

HCID 17788792N-[2-(3-cyanophenoxy)ethyl]-4-cyanobenzthioamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.46 g (5.00 mmol)) of N-[2-(3-cyanophenoxy)ethyl]-4-cyanobenzamide was dissolved in 50 ml of toluene. 3.03 g (7.5 mmol) of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide was added to the solution, and the obtained mixture was heated under reflux for 4 hours. The precipitate was removed by the filtration, and the solvent was evaporated under reduced pressure. The residue was purified by the silica gel column chromatography, and the title compound was obtained.

Workup

  1. temperaturethe obtained mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customThe precipitate was removed by the filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-1e97c0a040234ce3a4afe08aef55cf13
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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