Lawesson's reagent → (+/-)-5-[2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-1-methyl-3,4-dihydro-4-thioxo-2(1H)-pyrimidinone

HRID 324455Notes

Reaction equation

HRID 324455 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([C:16]3[C:17](=O)[NH:18][C:19](=[O:23])[N:20]([CH3:22])[CH:21]=3)[C:5]=2[N:6]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>O1CCOCC1>[CH3:1][C:2]1[O:3][C:4]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([C:16]3[C:17](=[S:34])[NH:18][C:19](=[O:23])[N:20]([CH3:22])[CH:21]=3)[C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 70112978HCID 70112978, compound

Product 1

HCID 88151745(+/-)-5-[2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-1-methyl-3,4-dihydro-4-thioxo-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product from step (iii), (0.075 g) and Lawesson's reagent (0.094 g) in 1,4-dioxane (5 ml) under nitrogen was heated at reflux 16 h. The reaction mixture was partitioned between ethyl acetate and saturated brine. The organic phase was collected, dried over magnesium sulphate and solvent evaporated under reduced pressure. Purification was by flash chromatogaphy eluting with 0 to 2% ethanol in dichloromethane followed by a second column eluting with 40% ethyl acetate in toluene to give the title compound as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux 16 h
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated brine
  4. customThe organic phase was collected
  5. dry with materialdried over magnesium sulphate and solvent
  6. customevaporated under reduced pressure
  7. customPurification
  8. washeluting with 0 to 2% ethanol in dichloromethane
  9. washeluting with 40% ethyl acetate in toluene

Sources & evidence

ORD record
ord-654ddbf7324c466d87ad38fb7851878f
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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