Lawesson's reagent → HCID 90070555, compound

HRID 590523Notes

Reaction equation

HRID 590523 reaction equation
[NH:1]1[C:5](=[O:6])[C:4]2([C:14]3[CH:13]=[CH:12][S:11][C:10]=3[CH2:9][CH2:8][CH2:7]2)[NH:3][C:2]1=O.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:25]2)=CC=1>O1CCOCC1>[S:25]=[C:2]1[NH:3][C:4]2([C:14]3[CH:13]=[CH:12][S:11][C:10]=3[CH2:9][CH2:8][CH2:7]2)[C:5](=[O:6])[NH:1]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 3870362spiro[6,7-dihydro-5H-1-benzothiophene-4,5'-imidazolidine]-2',4'-dione

Product 1

HCID 90070555HCID 90070555, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

6,7-Dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazolidine]-2′,5′-dione (0.5 g, 2.25 mmol) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson's reagent) (0.91 g, 2.25 mmol) were suspended in 1,4-dioxane (5 mL). The mixture was heated by microwave irradiation at 120° C. for 30 min. The solution was concentrated in vacuo and the crude residue purified on silica gel using a gradient elution of 20-100% ethyl acetate in 40-60 petroleum ether. Isolated material was further purified on silica gel using a gradient elution of 2-5% methanol in dichloromethane to afford the title compound as a colourless solid (0.54 g, 100%).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe crude residue purified on silica gel using
  3. washa gradient elution of 20-100% ethyl acetate in 40-60 petroleum ether
  4. customIsolated material was further purified on silica gel using
  5. washa gradient elution of 2-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-901a3b253b9a4e1ca1a877c5c9d35e3d
Source dataset
uspto-grants-2016_01
Patent number
US09233982B2

Reaction notes

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