Lawesson's reagent → HCID 58424222, compound

HRID 2096388Notes

Reaction equation

HRID 2096388 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[S:19][CH:20]=[CH:21][CH:22]=3)[O:8][C:5]2=[CH:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=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:32])[NH:12]3)[CH2:10][CH:9]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[O:8][C:5]2=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58423903HCID 58423903, compound

Product 1

HCID 58424222HCID 58424222, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 6-bromo-2-(thiophen-2-yl)spiro[chroman-4,4′-imidazolidine]-2′,5′-dione (135 mg, 0.357 mmol) and Lawesson's Reagent (144.3 mg, 0.357 mmol) in anhydrous 1,4-dioxane (4 mL) was heated under reflux for 24 h. The mixture was concentrated in vacuo and the residue was purified by preparative TLC to give 6-bromo-2-(thiophen-2-yl)-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (100 mg, 80%). 1H-NMR (CDCl3): 2.41 (m, 1H), 2.55 (dd, 1H), 6.04 (dd, 1H), 6.80 (d, 1H), 6.94 (t, 1H), 7.12 (d, 1H), 7.33 (m, 3H).

Workup

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

Sources & evidence

ORD record
ord-15599992d0c943f585968d091454f6a3
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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