Lawesson's reagent → HCID 86594481, compound

HRID 1986051Notes

Reaction equation

HRID 1986051 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:16]([C:17](=O)[CH:18]=2)=[CH:15][CH:14]=[C:13]([O:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:12]=3)=[CH:5][CH:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:16]([C:17](=[S:39])[CH:18]=2)=[CH:15][CH:14]=[C:13]([O:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:12]=3)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68886765HCID 68886765, compound

Product 1

HCID 86594481HCID 86594481, compoundYield 179.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 2-(4-methoxy-phenyl)-7-(3-morpholin-4-yl-propoxy)-chromen-4-one (200.0 mg, 0.51 mmol), Lawesson's reagent (122.7 mg, 0.30 mmol) and anhydrous toluene (3.5 mL) was refluxed under N2 for 1 hr. The solvent was removed under vacuum and the residue was purified by silica gel chromatography (EtOAc/MeOH/NEt3, 40/2/1) to give 2-(4-methoxy-phenyl)-7-(3-morpholin-4-yl-propoxy)-chromene-4-thione (222.0 mg, 100.0% yield) as a red solid and was used in next step without further purification. MS (ES+): m/e 412.1(M+H). HPLC/Method A (Rt 5.59 min, 74.0% purity).

Workup

  1. temperaturewas refluxed under N2 for 1 hr
  2. customThe solvent was removed under vacuum
  3. customthe residue was purified by silica gel chromatography (EtOAc/MeOH/NEt3, 40/2/1)

Sources & evidence

ORD record
ord-978ae1ab911f42b3b258e40a2932e9ef
Source dataset
uspto-grants-2009_06
Patent number
US07547794B2

Reaction notes

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