Lawesson's reagent → HCID 178470133, compound

HRID 1458946Notes

Reaction equation

HRID 1458946 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][C:8](=O)[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:6]2[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([SH:40])[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:6]2[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 22097611ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2(1H)-quinolone-3-carboxylate

Product 1

HCID 178470133HCID 178470133, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2(1H)-quinolone-3-carboxylate (6.8 g), Lawesson's reagent (8.0 g) and toluene (250 ml) was stirred under reflux for 18 hours. After cooling, the precipitated crystals were collected by filtration to give ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-mercaptoquinoline-3-carboxylate (5.0 g, 70%) which was then recrystallized from acetone. mp. 265°-266° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-7f3fe5a1d07740108998c9bc56a48268
Source dataset
uspto-grants-1998_12
Patent number
US05852039

Reaction notes

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