Lawesson's reagent → HCID 58423943, compound

HRID 2096422Notes

Reaction equation

HRID 2096422 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[NH:14][C:13](=O)[NH:12]3)[CH2:10][CH:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:8][C:5]2=[CH:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[NH:14][C:13](=[S:33])[NH:12]3)[CH2:10][CH:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:8][C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58423847HCID 58423847, compound

Product 1

HCID 58423943HCID 58423943, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-bromo-2-phenylspiro[chroman-4,4′-imidazolidine]-2′,5′-dione (440 mg, 1.18 mmol) in 1,4-dioxane (3.6 mL) in a 10 mL CEM microwave test tube was added Lawesson's reagent (477 mg, 1.18 mmol). The resulting mixture was heated in a CEM microwave reactor at 110° C. for 40 min and then cooled to room temperature. The solvent was removed in vacuo, and the residue was purified by flash chromatography to give 6-bromo-2-phenyl-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (238 mg, 52%). MS m/z 389 (M+H+).

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-24182ef315324c2680e7cb477c9dd1b1
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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