1,2-Dichloroethane → HCID 17975818, compound

HRID 2108881Notes

Reaction equation

HRID 2108881 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([SH:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[Cl:16][CH2:17][CH2:18]Cl.C([O-])([O-])=O.[K+].[K+].[OH-].[K+]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O>[Cl:16][CH2:17][CH2:18][S:13][C:7]1[C:6]2[C:11](=[CH:12][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:4][CH:5]=2)[N:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 178506078HCID 178506078, compound

Product 1

HCID 17975818HCID 17975818, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

7-Trifluoromethyl-4-quinoline-thiol (800 mg, 3.5 mmol) and 1,2-dichloroethane (10.4 g, 10.5 mmol) were charged in a 50 ml round-bottomed flask equipped with a magnetic stirrer. Then TBABr (600 mg, 1.7 mmol), K2CO3 (500 mg, 3.5 mmol), KOH (500 mg, 0.7 mmol) and water (2 mL) were added and the reaction mixture was stirred for 5 h at 20° C. The reaction mixture was poured in 100 mL of H2O and extracted with CH2Cl2 (150 mL). The organic layer was washed with water (30 mL), brine (2×10 mL), dried over MgSO4, filtered and evaporated at 30° C. to dryness. The crude compound was purified by column chromatography (SiO2; CH2Cl2:EtOAc=8:2 to 5:5) to give after evaporation 4-(2-chloroethylthio)-7-(trifluoromethyl)quinoline 30 (680 mg, 67% yield) as a beige solid.

Workup

  1. customequipped with a magnetic stirrer
  2. extractionextracted with CH2Cl2 (150 mL)
  3. washThe organic layer was washed with water (30 mL), brine (2×10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated at 30° C. to dryness
  7. customThe crude compound was purified by column chromatography (SiO2; CH2Cl2:EtOAc=8:2 to 5:5)
  8. customto give

Sources & evidence

ORD record
ord-07e962db914e4c539de9efc3b7bdf908
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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