Lawesson's reagent → 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline-6-thiol

HRID 341843Notes

Reaction equation

HRID 341843 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16](O)[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C1(C)C(C)=CC=CC=1>[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16]([SH:31])[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 98604535,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol

Product 1

HCID 158384715,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline-6-thiolYield 30.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A portion (5.55 g) of 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol obtained in Example 4 was suspended in xylene (700 mL); following the addition of a Lawesson reagent (4.04 g), the suspension was heated under reflux for 30 min under an argon atmosphere. After standing to cool, the supernatant was concentrated under vacuum and the residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate) to yield the titled compound as colorless crystals (0.91 g).

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 30 min under an argon atmosphere
  3. temperatureto cool
  4. concentrationthe supernatant was concentrated under vacuum
  5. customthe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate)

Sources & evidence

ORD record
ord-507ae99047eb43cba06871e3f86b754e
Source dataset
uspto-grants-1999_01
Patent number
US05856334

Reaction notes

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