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

HRID 241998Notes

Reaction equation

HRID 241998 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:23]=[CH:22][CH:21]=[N:20]3)=[CH:15][CH:14]=2)[N:4]=[C:3]1[C:24]([O:26][CH2:27][CH3:28])=[O:25].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>C1(C)C=CC=CC=1>[N:19]1([C:16]2[CH:15]=[CH:14][C:13]([CH2:12][N:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:2](=[S:38])[C:3]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N:4]3)=[CH:18][CH:17]=2)[CH:23]=[CH:22][CH:21]=[N:20]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68797180ethyl 4-oxo-1-[4-(1H-pyrazol-1-yl)benzyl]-1,4-dihydrocinnoline-3-carboxylate

Product 1

HCID 86659984ethyl 1-[4-(1H-pyrazol-1-yl)benzyl]-4-thioxo-1,4-dihydrocinnoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 4-oxo-1-[4-(1H-pyrazol-1-yl)benzyl]-1,4-dihydrocinnoline-3-carboxylate (750 mg, 2.00 mmol) was dissolved in toluene (9 mL), sparged under nitrogen and treated with Lawesson's Reagent (486 mg, 1.20 mmol, 0.6 equiv). The mixture was placed into an oil bath preheated to 105° C. for 1 hour, cooled to ambient temperature and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 60:40; hexanes:ethyl acetate) to provide the titled compound as a dark green solid.

Workup

  1. customsparged under nitrogen
  2. customThe mixture was placed into an oil bath
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel gradient chromatography (100:0 to 60:40; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-f2f4963f7ca04fb182266f2a9dabe8aa
Source dataset
uspto-grants-2014_02
Patent number
US08653079B2

Reaction notes

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