Lawesson's reagent → 1-(6-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-betacarbolin-2-yl)-1-ethane-thione

HRID 1004065Notes

Reaction equation

HRID 1004065 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:35](=[CH:36][CH:37]=1)[NH:34][C:33]1[CH:32]([CH3:38])[N:31]([C:39](=O)[CH3:40])[CH2:30][CH2:29][C:28]2=1>C1(C)C=CC=CC=1>[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33]1[CH:32]([CH3:38])[N:31]([C:39](=[S:10])[CH3:40])[CH2:30][CH2:29][C:28]2=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 18328986HCID 18328986, compound

Product 1

HCID 187942441-(6-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-betacarbolin-2-yl)-1-ethane-thioneYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Lawesson's reagent (520 mg) is added portionwise, at 110° C., to a solution of 1-(6-methoxy-1-methyl-2,3,4,9-tetrahydro- 1H-β-carbolin-2-yl)-1 -ethanone (500 mg) in anhydrous toluene (25 mL). After refluxing for 1 h and evaporation of the toluene, the product is chromatographed on silica gel (99/1 chlorofomvmethanol eluent) and the 1-(6-methoxy-1-methyl-2,3,4,9-tetrahydro- 1H-β-carbolin-2-yl)-1 -ethanethione is thus recovered (40% yield).

Workup

  1. temperatureAfter refluxing for 1 h
  2. customevaporation of the toluene
  3. customthe product is chromatographed on silica gel (99/1 chlorofomvmethanol eluent)
  4. customthe 1-(6-methoxy-1-methyl-2,3,4,9-tetrahydro- 1H-β-carbolin-2-yl)-1 -ethanethione is thus recovered (40% yield)

Sources & evidence

ORD record
ord-b6ed1ac5046e4c32bf52451fc7c74ad4
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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