Lawesson's reagent → HCID 58423943, compound

HRID 2096450Notes

Reaction equation

HRID 2096450 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 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 6-bromo-2-phenylspiro[chroman-4,4′-imidazolidine]-2′,5′-dione (1.12 g, 3 mmol) and Lawesson's Reagent (1.21 g, 3 mmol) in dry 1,4-dioxane (25 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-phenyl-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (780 mg, 67%). 1H-NMR (CDCl3): 2.26 (dd, 1H), 2.43 (dd, 1H), 5.76 (dd, 1H), 6.84 (m, 2H), 7.32-7.36 (m, 6H), 8.22 (m, 1H).

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-cffd4c3c5b2c4f0b8b9a596fc7800350
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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