Hantzsch ester → HCID 86613959, compound

HRID 1811458Notes

Reaction equation

HRID 1811458 reaction equation
[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:17]3[C:12](=[C:13]([CH:18]=[C:19]4[S:23][C:22](=[S:24])[NH:21][C:20]4=[O:25])[CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:26])=[CH:3][CH:2]=1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>C1(C)C=CC=CC=1>[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:2]=[CH:3][C:4]([CH2:7][N:8]2[C:17]3[C:12](=[C:13]([CH2:18][CH:19]4[S:23][C:22](=[S:24])[NH:21][C:20]4=[O:25])[CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:26])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70849Hantzsch esterHCID 86613957HCID 86613957, compound

Product 1

HCID 86613959HCID 86613959, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 20 ml of toluene were added 1.4 g of 1-(biphenyl-4-ylmethyl)-5-(4-oxo-2-thioxothiazolidine-5-ylidenemethyl)-3,4-dihydro-1H-quinolin-2-one, 1.01 g of diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine dicarboxylate, and 1.4 g of silica gel, followed by heating and refluxing overnight. The solvent was distilled off, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1→2:1). The purified product was recrystallized from toluene, giving 0.84 g (60% yield) of 1-(biphenyl-4-ylmethyl)-5-(4-oxo-2-thioxothiazolidin-5-ylmethyl)-3,4-dihydro-1H-quinolin-2-one as a white powder.

Workup

  1. temperatureby heating
  2. temperaturerefluxing overnight
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1→2:1)
  5. customThe purified product was recrystallized from toluene

Sources & evidence

ORD record
ord-869e58a52c9d401ea848c25998800f2f
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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