Water → Methyl 4'-[(3-butyl-1,4-dihydro-4-thioxo-1-quinolinyl)-methyl](1,1'-biphenyl)-2-carboxylate

HRID 1602935Notes

Reaction equation

HRID 1602935 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH2:23]([C:27]1[C:36](=O)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([C:45]3[C:46]([C:51]([O:53][CH3:54])=[O:52])=[CH:47][CH:48]=[CH:49][CH:50]=3)=[CH:41][CH:40]=2)[CH:28]=1)[CH2:24][CH2:25][CH3:26].O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:23]([C:27]1[C:36](=[S:10])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([C:45]3[C:46]([C:51]([O:53][CH3:54])=[O:52])=[CH:47][CH:48]=[CH:49][CH:50]=3)=[CH:41][CH:40]=2)[CH:28]=1)[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 19608515Methyl 4'-[(3-butyl-1,4-dihydro-4-oxo-1-quinolinyl)-methyl](1,1'-biphenyl)-2-carboxylate

Product 1

HCID 19608518Methyl 4'-[(3-butyl-1,4-dihydro-4-thioxo-1-quinolinyl)-methyl](1,1'-biphenyl)-2-carboxylateYield 26,169.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.10 mg of Lawesson reagent were added to a solution of 400 mg of the product of Example 3 in 20 ml of toluene and the mixture was refluxed for 90 minutes. The mixture was poured into 100 ml of water and extraction was carried out with ethyl acetate. Th extracts were washed with water, dried, filtered and evaporated to dryness to obtain 0.6 g of the expected product which was chromatographed on silica (eluant: methylene chloride-acetone (98-2)) to collect 0.42 g of the desired product melting at 158° C.

Workup

  1. temperaturethe mixture was refluxed for 90 minutes
  2. washTh extracts were washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f22d7c889e74403c910ba11a563cf17e
Source dataset
uspto-grants-1999_11
Patent number
US05985894

Reaction notes

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