Lawesson's reagent → HCID 58424626, compound

HRID 1408628Notes

Reaction equation

HRID 1408628 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]([F: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]([F:24])[CH:19]=3)[O:8][C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58423922HCID 58423922, compound

Product 1

HCID 58424626HCID 58424626, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 6-bromo-2-(3-fluorophenyl)spiro[chroman-4,4′-imidazolidine]-2′,5′-dione (300 mg, 0.77 mmol) and Lawesson's reagent (312 mg, 0.77 mmol) in dry 1,4-dioxane (10 mL) was refluxed for 24 h. The mixture was concentrated in vacuo and the residue was purified by preparative TLC to give 6-bromo-2-(3-fluorophenyl)-2′-thioxospiro[chroman-4,4′-imidazolidine]-5′-one (35 mg, 17%).

Workup

  1. temperaturewas refluxed for 24 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-2150cd87282b4dabb338fa737d6726b1
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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