Lawesson's reagent → 3-[4-[[3,5-Bis(trimethylsilyl)benzenecarbothioyl]amino]phenyl]propanoic acid

HRID 2265118Notes

Reaction equation

HRID 2265118 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][Si:24]([CH3:52])([CH3:51])[C:25]1[CH:26]=[C:27]([CH:44]=[C:45]([Si:47]([CH3:50])([CH3:49])[CH3:48])[CH:46]=1)[C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][C:39]([O:41]CC)=[O:40])=[CH:33][CH:32]=1)=O>C1(C)C=CC=CC=1>[CH3:23][Si:24]([CH3:52])([CH3:51])[C:25]1[CH:26]=[C:27]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[CH:33][CH:32]=2)=[S:10])[CH:44]=[C:45]([Si:47]([CH3:50])([CH3:49])[CH3:48])[CH:46]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68485079Ethyl 3-[4-[[3,5-bis(trimethylsilyl)benzoyl]amino]phenyl]propanoate

Product 1

HCID 594462833-[4-[[3,5-Bis(trimethylsilyl)benzenecarbothioyl]amino]phenyl]propanoic acidYield 131.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Lawesson's reagent (90 mg) was added to a toluene (5 ml) solution of Compound 20a (140 mg). The obtained mixture was stirred at 100° C. in a nitrogen atmosphere for 1 hour. After the reaction was over, the reaction mixture was allowed to cool, and concentrated. The obtained residue was purified by column chromatography (5% ethyl acetate/n-hexane). Fractions containing the ester body of Compound 4 were collected, and concentrated to dryness. As a result, 126 mg of yellow solid was obtained. The obtained yellow solid (90 mg) was, without further purification, dissolved in ethanol (1 ml). A 1N sodium hydroxide aqueous solution (1 ml) was added thereto in a nitrogen atmosphere. The obtained mixture was stirred under heating at 45° C. for 1 hour. After the reaction was over, the mixture was allowed to cool, and a 1N hydrochloric acid aqueous solution was added thereto. 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 20 (54 mg, 64%) was obtained as an opalescent solid.

Workup

  1. temperatureto cool
  2. concentrationconcentrated
  3. customThe obtained residue was purified by column chromatography (5% ethyl acetate/n-hexane)
  4. additionFractions containing the ester body of Compound 4
  5. customwere collected
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-92fd1948aa9740959ae7ec5bcd860bca
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

Loading…