Lawesson's reagent → HCID 86662687, compound

HRID 242032Notes

Reaction equation

HRID 242032 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[C:5]([CH3:16])=[C:4]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:3]1=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1.CCOC(C)=O.CCCCCC>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[C:5]([CH3:16])=[C:4]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:3]1=[S:32]

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 21226206Ethyl acetate hexaneHCID 66776512HCID 66776512, compound

Product 1

HCID 86662687HCID 86662687, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 460 mg (1.5 mmol) ethyl 1,4-dimethyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylate in toluene (10 ml) was treated with 2.4 g (5.9 mmol) Lawesson's reagent at RT, followed by heating to 120° C. for 16 h. After cooling to RT the RS was quenched with a sat. aq. Na2CO3 solution (30 ml). The mixture was then extracted with EtOAc (3×30 ml). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. CC (EtOAc/hexane 1:4) of the residue provided 400 mg (1.2 mmol, 82%) ethyl 1,4-dimethyl-2-thioxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylate.

Workup

  1. temperatureAfter cooling to RT the RS
  2. customwas quenched with a sat. aq. Na2CO3 solution (30 ml)
  3. extractionThe mixture was then extracted with EtOAc (3×30 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ac1a85a87bc4dc4af7c4976d4defeca
Source dataset
uspto-grants-2014_02
Patent number
US08653102B2

Reaction notes

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