Lawesson's reagent → ethyl-8-chloro-1-[4-(1H-pyrazol-1-yl)benzyl]-4-thioxo-1,4-dihydrocinnoline-3-carboxylate

HRID 449972Notes

Reaction equation

HRID 449972 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([Cl:17])[CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[CH:28][CH:27]=[N:26]3)=[CH:21][CH:20]=2)[N:7]=1)=[O:5])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[S:39])[C:14]2[C:9](=[C:10]([Cl:17])[CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[CH:28][CH:27]=[N:26]3)=[CH:21][CH:20]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86659993Ethyl-8-chloro-4-oxo-1-[4-(1H-pyrazol-1-yl)benzyl]-1,4-dihydrocinnoline-3-carboxylate

Product 1

HCID 86659992ethyl-8-chloro-1-[4-(1H-pyrazol-1-yl)benzyl]-4-thioxo-1,4-dihydrocinnoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl-8-chloro-4-oxo-1-[4-(1H-pyrazol-1-yl)benzyl]-1,4-dihydrocinnoline-3-carboxylate (627 mg, 1.53 mmol) was dissolved in toluene (7 mL), treated with Lawesson's Reagent (434 mg, 1.074 mmol, 0.7 equiv) and placed into an oil bath preheated at 105° C. for 5 minutes. The mixture was cooled to ambient temperature, concentrated in vacuo and the residue was purified by silica gel gradient chromatography (100:0 to 60:40; hexanes:ethyl acetate), providing the titled compound.

Workup

  1. customplaced into an oil bath
  2. concentrationconcentrated in vacuo
  3. customthe residue was purified by silica gel gradient chromatography (100:0 to 60:40; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-234cf147a302483788cd55520e241f98
Source dataset
uspto-grants-2013_07
Patent number
US08486946B2

Reaction notes

Loading…