Water → 3-Ethoxycarbonyl-4-(3-trifluoromethylphenylmercapto)-6-trifluoromethylquinoline

HRID 266072

Reaction equation

HRID 266072 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[F:21][C:22]([F:31])([F:30])[C:23]1[CH:24]=[C:25]([SH:29])[CH:26]=[CH:27][CH:28]=1.C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[CH2:19]([O:18][C:16]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[S:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:21])([F:30])[F:31])[CH:24]=1)=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=2)=[O:17])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1367513-(Trifluoromethyl)benzenethiolHCID 4322147Ethyl 4-chloro-6-(trifluoromethyl)quinoline-3-carboxylate

Product 1

HCID 545681733-Ethoxycarbonyl-4-(3-trifluoromethylphenylmercapto)-6-trifluoromethylquinolineYield 34.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction mixture of 151.8 mg (0.50 mmol) of 4-chloro-3-ethoxycarbonyl-6-trifluoromethylquinoline, 106.9 mg (0.60 mmol) of 3-trifluoromethylthiophenol and 100 μL of diisopropylethylamine in 2.0 mL of N,N-dimethylformamide was stirred at room temperature for 2 h and cooled. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulphate and concentrated. The resulting residue was purified on silica gel column eluting with ethyl acetate-hexane (1:3) to give 76.4 mg (34%) of the title compound.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe resulting residue was purified on silica gel column
  7. washeluting with ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-89d643ace9cf4609840cf2e48ca6a599
Source dataset
uspto-grants-1997_07
Patent number
US05650415

Linked notes

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