Lawesson's reagent → 8-Cyano-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinoline-4-thione

HRID 1937005Notes

Reaction equation

HRID 1937005 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=O)[CH:7]3[CH2:14][CH2:15][CH2:16][CH:6]3[C:5]=2[CH:4]=1)#[N:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>COCCOC>[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[S:26])[CH:7]3[CH2:14][CH2:15][CH2:16][CH:6]3[C:5]=2[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 22462459HCID 22462459, compound

Product 1

HCID 224624558-Cyano-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinoline-4-thione

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

8-Cyano-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one (70 mg, 0.33 mmol) is heated to 80° C. with Lawesson's reagent (146 mg, 0.36 mmol) for 2 hours in DME (20 ml). The batch is concentrated by evaporation and purified by column chromatography (SiO2) with ethyl acetate-hexane: 50 mg (66%) of product.

Workup

  1. concentrationThe batch is concentrated by evaporation
  2. custompurified by column chromatography (SiO2) with ethyl acetate-hexane

Sources & evidence

ORD record
ord-1b5d455f0c6a4eee847d9d5c64da65a6
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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