Lawesson's reagent → 5,7-dimethoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinethione

HRID 130331Notes

Reaction equation

HRID 130331 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=O)[N:6]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH:7]=[N:8]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[S:33])[N:6]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH:7]=[N:8]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 116881915,7-Dimethoxy-3-(4-methoxyphenyl)quinazoline-4-one

Product 1

HCID 116168585,7-dimethoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinethioneYield 72.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of 5,7-dimethoxy-3-(4-methoxyphenyl)-quinazoline-4-one (240 mg, 0.76 mmol), as prepared in Example 18 or 19, and Lawesson's reagent (310 mg, 0.76 mmol) in toluene (4 mL) was refluxed overnight. The mixture was evaporated to dryness. EtOAc was added and the mixture was washed with water, brine and dried over MgSO4. Evaporation gave a crude solid. Purification was performed by flash chromatography on silica gel, loaded with dichloromethane and eluted with 45% ethyl acetate in hexane. The pure fraction was combined and evaporated to give a yellow foam (180 mg, 72%).

Workup

  1. temperaturewas refluxed overnight
  2. customThe mixture was evaporated to dryness
  3. additionEtOAc was added
  4. washthe mixture was washed with water, brine
  5. dry with materialdried over MgSO4
  6. customEvaporation
  7. customgave a crude solid
  8. customPurification
  9. washeluted with 45% ethyl acetate in hexane
  10. customevaporated

Sources & evidence

ORD record
ord-1f39228b75864094858097c95307b743
Source dataset
uspto-grants-2008_06
Patent number
US07381730B2

Reaction notes

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