Lawesson's reagent → (+/-)-1-Methyl-5-(2-methyl-7-ethyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-3,4-dihydro-4-thioxo-2-(1H)-pyrimidinone

HRID 324465Notes

Reaction equation

HRID 324465 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:16]([C:17]3[C:18](=O)[NH:19][C:20](=[O:24])[N:21]([CH3:23])[CH:22]=3)[C:11]3[N:12]=[C:13]([CH3:15])[S:14][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:26]=1)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>O1CCOCC1>[CH3:23][N:21]1[CH:22]=[C:17]([CH:16]2[C:11]3[N:12]=[C:13]([CH3:15])[S:14][C:10]=3[CH:9]=[CH:8][C:7]3[CH:26]=[C:3]([CH2:1][CH3:2])[CH:4]=[CH:5][C:6]2=3)[C:18](=[S:36])[NH:19][C:20]1=[O:24]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 70113042(+/-)-5-[7-Ethyl-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl]-1-methyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 88151787(+/-)-1-Methyl-5-(2-methyl-7-ethyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-3,4-dihydro-4-thioxo-2-(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product of step (xii) (0.070 g) and Lawesson's reagent (0.077 g) in 1,4-dioxane (5 ml) was heated at reflux for 16 hours. The solvent was evaporated under reduced pressure. Purification was by chromatography eluting with 2% ethanol in dichloromethane to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customPurification
  5. washeluting with 2% ethanol in dichloromethane

Sources & evidence

ORD record
ord-a022612c47b944778eaa5be81911e400
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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