Water → HCID 88228749, compound

HRID 617396Notes

Reaction equation

HRID 617396 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][O:24][CH:25]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36]/[N:37]=[C:38](\[CH3:46])/[C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1)[C:26]([NH:28][CH3:29])=O.O>C1(C)C=CC=CC=1>[CH3:23][O:24][CH:25]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36]/[N:37]=[C:38](\[CH3:46])/[C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1)[C:26]([NH:28][CH3:29])=[S:10]

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 88229995HCID 88229995, compound

Product 1

HCID 88228749HCID 88228749, compoundYield 137.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Lawesson's reagent (40 mg, 0.1 mmol) was added to a solution of (E)-α-methoxy-N-methyl-2-(α-methyl-4-chloro-benzylideneaminooxy)phenylacetamide (73 mg, 0.2 mmol) in toluene (3 ml), and the mixture was heated at 80° C. for 1.5 hours with stirring. The mixture was cooled to room temperature. Water was added, and the mixture was extracted with ether and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=4/1) to give the desired compound (E)-α-methoxy-N-methyl-2-(α-methyl-4-chlorobenzylideneaminooxy)phenylthioacetamide (50 mg, 66%) as an oil.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ether
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-9b0a1aa97c3d48de8f8f2de949ff2630
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

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