Lawesson's reagent → HCID 58424072, compound

HRID 1408618Notes

Reaction equation

HRID 1408618 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][C:9]([CH3:24])([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: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][C:9]([CH3:24])([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 58424692HCID 58424692, compound

Product 1

HCID 58424072HCID 58424072, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 6-bromo-2-methyl-2-phenylspiro[chroman-4,4′-imidazolidine]-2′,5′-dione (1.16 g, 3 mmol) and Lawesson's Reagent (1.21 g, 3 mmol) in dry 1,4-dioxane (24 mL) was refluxed for 24 h. The mixture was concentrated in vacuo and the residue was purified by column to give 6-bromo-2-methyl-2-phenyl-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (748 mg, 61%). 1H-NMR (CDCl3): 1.75 (s, 3H), 3.78 (m, 2H), 5.79 (s, 1H), 6.94 (m, 1H), 7.14 (m, 1H), 7.22 (m, 1H), 7.26-7.53 (m, 5H), 8.39 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-438f384e54ee4c6d86e5c1235c85f1a7
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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