Lawesson's reagent → HCID 58424170, compound

HRID 1408650Notes

Reaction equation

HRID 1408650 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][C:21]([Cl:24])=[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: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][C:21]([Cl:24])=[CH:20][CH:19]=3)[O:8][C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58423849HCID 58423849, compound

Product 1

HCID 58424170HCID 58424170, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-bromo-2-(4-chlorophenyl)spiro[chroman-4,4′-imidazolidine]-2′,5′-dione (600 mg, 1.48 mmol) and Lawesson's Reagent (596 mg, 1.48 mmol) in 1,4-dioxane (25 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-(4-chlorophenyl)-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (450 mg, 69%). 1H-NMR (MeOD): 2.24 (m, 1H), 2.45 (m, 1H), 6.82 (m, 1H), 6.91 (m, 1H), 7.20 (m, 1H), 7.44 (m, 5H).

Workup

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

Sources & evidence

ORD record
ord-e98547523c354369a123c52cefbd7bb7
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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