Lawesson's reagent → HCID 11500537, compound

HRID 2056615Notes

Reaction equation

HRID 2056615 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH:33][C:34](=O)[C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=2[F:42])[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=1>C1(C)C=CC=CC=1>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH:33][C:34]([C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=2[F:42])=[S:10])[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 7960855HCID 7960855, compound

Product 1

HCID 11500537HCID 11500537, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

20.3 g (50 mmol; 1.5 equivalents) of Lawesson's reagent is added to 9.8 g (33.4 mmol) of N-(3,5-dimethoxyphenyl)-2,6-difluorobenzamide in solution in 150 ml of anhydrous toluene. The reaction medium is maintained under stirring at 120° C. for 8 hours, then, after returning to ambient temperature, is washed with 3 times 75 ml of water. The resulting organic phase is dried over magnesium sulphate then the solvent is evaporated off under reduced pressure. The residue is purified by chromatography on a silica column (eluent: dichloromethane/methanol 98/2) and the expected product is obtained in the form of a green oil (10 g; yield=96%).

Workup

  1. temperatureThe reaction medium is maintained
  2. customafter returning to ambient temperature
  3. washis washed with 3 times 75 ml of water
  4. dry with materialThe resulting organic phase is dried over magnesium sulphate
  5. customthe solvent is evaporated off under reduced pressure
  6. customThe residue is purified by chromatography on a silica column (eluent: dichloromethane/methanol 98/2)

Sources & evidence

ORD record
ord-ce50ae30fd7b4f8781a6e1b7993afe9b
Source dataset
uspto-grants-2008_02
Patent number
US07335674B2

Reaction notes

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