Lawesson's reagent → 2-[[5-{5H-Dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2-oxo-4-thioxo-1(2H)-pyrimidinyl]methyl]-4-thiazolecarboxylic acid, ethyl ester

HRID 1275879Notes

Reaction equation

HRID 1275879 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16]3[C:17](=O)[NH:18][C:19](=[O:33])[N:20]([CH2:22][C:23]4[S:24][CH:25]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=4)[CH:21]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:44])=CC=1>O1CCOCC1.C(OCC)(=O)C>[CH:3]1[C:4]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16]3[C:17](=[S:44])[NH:18][C:19](=[O:33])[N:20]([CH2:22][C:23]4[S:24][CH:25]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:27]=4)[CH:21]=3)[C:5]=2[CH:11]=[CH:1][CH:2]=1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 117334062-[[5-{5H-Dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-4-thiazolecarboxylic acid, ethyl ester

Product 1

HCID 867561222-[[5-{5H-Dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2-oxo-4-thioxo-1(2H)-pyrimidinyl]methyl]-4-thiazolecarboxylic acid, ethyl ester

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product of step (iv) (2.1 g) and Lawesson's reagent (1.78 g) in dry 1,4-dioxane (36 ml) was heated at reflux for 16 hours. After cooling, the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 50% ethyl acetate in isohexane. Yield 1.5 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. temperatureAfter cooling
  4. washwashed with water
  5. customevaporated under reduced pressure
  6. customPurification
  7. washeluting with 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-6e0b58f8a4254d629a76e3e528c4cef4
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

Loading…