Lawesson's reagent → HCID 86644387, compound

HRID 1882342Notes

Reaction equation

HRID 1882342 reaction equation
[C:1]1([NH:7][C:8](=O)[CH2:9][CH:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>O1CCOCC1>[C:1]1([NH:7][C:8](=[S:35])[CH2:9][CH:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86644388HCID 86644388, compound

Product 1

HCID 86644387HCID 86644387, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To N-phenyl-3,3-bis(phenylthio)propionamide (0.90 g) were added Lawesson's reagent (2.0 g) and 1,4-dioxane (20 mL), and the mixture was heated to reflux for 1.5 hours. The reaction mixture was left to cool to room temperature, and then concentrated under reduced pressure. The residue was isolated and purified by medium pressure preparative liquid chromatography (YAMAZEN SI-40B, hexane:ethyl acetate=3:1) to obtain N-phenyl-3,3-bis(phenylthio)thiopropionamide (0.69 g) as an orange oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. waitThe reaction mixture was left
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was isolated
  6. custompurified by medium pressure preparative liquid chromatography (YAMAZEN SI-40B, hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-fb9cf9e432cd4720b176d47bba1ddac7
Source dataset
uspto-grants-2012_11
Patent number
US08318981B2

Reaction notes

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