Lawesson's reagent → HCID 86755647, compound

HRID 1871966Notes

Reaction equation

HRID 1871966 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[N:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:25][CH:24]=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>[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](=[S:44])[NH:18][C:19](=[O:33])[N:20]([CH2:22][C:23]4[N:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:25][CH:24]=4)[CH:21]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86755646HCID 86755646, compound

Product 1

HCID 86755647HCID 86755647, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product from step (v) (1.84 g) and Lawesson's reagent (1.65 g) in 1,4-dioxane (30 ml) was heated at reflux for 24 hours. The mixture was partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic phase was dried (MgSO4) and evaporated. Purification was by chromatography eluting with 50% ethyl acetate in isohexane. Yield 1.38 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customThe mixture was partitioned between ethyl acetate and aqueous sodium bicarbonate
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. customPurification
  7. washeluting with 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-53bd5d02dd0f4b8486689564fd6dbf3e
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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