Lawesson's reagent → HCID 9796811, compound

HRID 1004053Notes

Reaction equation

HRID 1004053 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:33]3[CH2:34][CH2:35][N:36]4[C:41]([C:32]=3[NH:31][C:28]2=[CH:29][CH:30]=1)=[C:40]([CH2:42][CH3:43])[CH2:39][CH2:38][C:37]4=O>C1(C)C=CC=CC=1>[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:33]3[CH2:34][CH2:35][N:36]4[C:41]([C:32]=3[NH:31][C:28]2=[CH:29][CH:30]=1)=[C:40]([CH2:42][CH3:43])[CH2:39][CH2:38][C:37]4=[S:10]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 99042661-Ethyl-2,6,7,12-tetrahydro-9-methoxyindolo[2,3-a]quinolizin-4(3H)-one

Product 1

HCID 9796811HCID 9796811, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Lawesson's reagent (0.5 nimol) is added portionwise, at 110° C., to a solution of 9-metlioxy-1-ethyl-2,3,4,6,7,12-hexahydroindolo[2,3-a]quinoIizin-4-one (300 mg, 1.01 mmol) in anhydrous toluene (15 mL). After refluxing for 30 min. and evaporation of the toluene, the product is chromatographed on silica gel (99/1 chloroform/methanol eluent) and 9-methoxy-1-ethyl-2,3,4,6,7,12-hexahydroindolo[2,3-alquinolizine-4-thione is thus recovered (60% yield).

Workup

  1. temperatureAfter refluxing for 30 min.
  2. customevaporation of the toluene
  3. customthe product is chromatographed on silica gel (99/1 chloroform/methanol eluent) and 9-methoxy-1-ethyl-2,3,4,6,7,12-hexahydroindolo[2,3-alquinolizine-4-thione
  4. customis thus recovered (60% yield)

Sources & evidence

ORD record
ord-d735f1881c4f4a23a0b5bfdb47a32517
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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