Lawesson's reagent → HCID 58423962, compound

HRID 2096436Notes

Reaction equation

HRID 2096436 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]=[C:20]([Cl:24])[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:34])=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:34])[NH:12]3)[CH2:10][CH:9]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[O:8][C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58424500HCID 58424500, compound

Product 1

HCID 58423962HCID 58423962, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-bromo-2-(3-chlorophenyl)spiro[chroman-4,4′-imidazolidine]-2′,5′-dione (470 mg, 1.16 mmol) and Lawesson's Reagent (468 mg, 1.16 mmol) in 1,4-dioxane (16 mL) was stirred at 110° C. overnight. The solvent was removed in vacuo and the residue was purified by preparative TLC to give 6-bromo-2-(3-chlorophenyl)-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (350 mg, 71%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-2b75685515db42ed8b26079fbfa8fa07
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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