Lawesson's reagent → HCID 58424060, compound

HRID 1408801Notes

Reaction equation

HRID 1408801 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]12[C:21](=[O:22])[NH:20][C:19](=O)[NH:18]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:9](=[CH:10][CH:11]=1)[S:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]12[C:21](=[O:22])[NH:20][C:19](=[S:33])[NH:18]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58424802HCID 58424802, compound

Product 1

HCID 58424060HCID 58424060, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6′-bromo-2′-phenylspiro[imidazolidine-4,4′-thiochroman]-2,5-dione (237 mg, 0.61 mmol) and Lawesson's reagent (246 mg, 0.61 mmol) in 1,4-dioxane (3 mL) in a 10 mL CEM microwave test tube is heated in a CEM microwave reactor at 110° C. for 30 min. After cooled to rt, the solvent is removed in vacuo, and the residue is purified by flash chromatography column to give 6′-bromo-2′-phenyl-2-thioxospiro[imidazolidine-4,4′-thiochroman]-5-one (200 mg, 81%). MS ESI+ve m/z 405 (M+H)+.

Workup

  1. customthe solvent is removed in vacuo
  2. customthe residue is purified by flash chromatography column

Sources & evidence

ORD record
ord-d06638641fe24f75b30ef2ccc573a82d
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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