Lawesson's reagent → HCID 86658454, compound

HRID 1515379Notes

Reaction equation

HRID 1515379 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[Si:23]([O:40][CH2:41][CH2:42][CH2:43]/[C:44](=[CH:54]\[S:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)/[C:45]([NH:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=O)([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O.C(=O)(O)[O-].[Na+]>O1CCCC1>[Si:23]([O:40][CH2:41][CH2:42][CH2:43]/[C:44](=[CH:54]\[S:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)/[C:45](=[S:10])[NH:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:36]([CH3:38])([CH3:37])[CH3:39])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 67425928HCID 67425928, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 86658454HCID 86658454, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lawesson reagent was added to tetrahydrofuran solution including 2.81 g of (E)-5-(tert-butyldiphenylsilyloxy)-N-phenyl-2-(phenylthiomethylene)pentanamide. The resulting solution was heated under reflux for one night and cooled to room temperature, followed by adding saturated sodium bicarbonate water to extract. The water layer was extracted with ethyl acetate, and the organic layer was mixed and dried with anhydrous magnesium sulfate, then filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.17 g of the title compound.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for one night
  3. extractionto extract
  4. extractionThe water layer was extracted with ethyl acetate
  5. additionthe organic layer was mixed
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-568701c19ba942f185d4b3d1b9cdc1ff
Source dataset
uspto-grants-2012_07
Patent number
US08222430B2

Reaction notes

Loading…