Lawesson's reagent → HCID 59446284, compound

HRID 2265116Notes

Reaction equation

HRID 2265116 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][Si:24]([CH3:53])([CH3:52])[C:25]1[CH:26]=[C:27]([CH:45]=[C:46]([Si:48]([CH3:51])([CH3:50])[CH3:49])[CH:47]=1)[C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34](/[C:37](/[CH3:44])=[CH:38]/[C:39]([O:41]CC)=[O:40])=[CH:33][CH:32]=1)=O>C1(C)C=CC=CC=1>[CH3:23][Si:24]([CH3:53])([CH3:52])[C:25]1[CH:26]=[C:27]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34](/[C:37](/[CH3:44])=[CH:38]/[C:39]([OH:41])=[O:40])=[CH:33][CH:32]=2)=[S:10])[CH:45]=[C:46]([Si:48]([CH3:51])([CH3:50])[CH3:49])[CH:47]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86761243HCID 86761243, compound

Product 1

HCID 59446284HCID 59446284, compoundYield 168.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Lawesson's reagent (134 mg) was added to a toluene (5 ml) solution of Compound 19c (300 mg), and the obtained mixture was stirred while refluxing under heating for 20 minutes. After the mixture was allowed to cool, the solvent was distilled off. The obtained residue was purified by column chromatography (6.25% ethyl acetate/n-hexane). Fractions containing the ester body of Compound 19 were collected and concentrated to dryness. As a result, 246 mg of yellow solid was obtained. The obtained yellow solid was, without further purification, dissolved in ethanol (10 ml), and a 2N sodium hydroxide aqueous solution (2.62 ml) was added thereto in a nitrogen atmosphere. The obtained mixture was stirred under heating at 70° C. for 2 hours. After the reaction was over, the mixture was allowed to cool. A 2N hydrochloric acid aqueous solution was added thereto, and the mixture was separated with ethyl acetate and water. The organic layer was washed once with water and once with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and as a result, Compound 19 (112 mg, 48%) was obtained as a yellow solid.

Workup

  1. temperaturewhile refluxing
  2. temperatureunder heating for 20 minutes
  3. temperatureto cool
  4. distillationthe solvent was distilled off
  5. customThe obtained residue was purified by column chromatography (6.25% ethyl acetate/n-hexane)
  6. additionFractions containing the ester body of Compound 19
  7. customwere collected
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a778ad5caec04b65b80b70901f2c2426
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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