Sodium ethanethiolate → HCID 58615381, compound

HRID 853014Notes

Reaction equation

HRID 853014 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.[S-:13][CH2:14][CH3:15].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[S:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 51395376-Bromo-4-chloroquinoline

Product 1

HCID 58615381HCID 58615381, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-4-chloro-quinoline (1.5 g, 6.18 mmol) in DMF (60 mL) was added sodium thioethoxide (624 mg, 7.42 mmol) at 0° C. After addition, it was turned to a dark green solution which then turned to a yellow cloudy solution after 15 h at room temperature. Then, the mixture was diluted with water and extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine solution and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the filtrate was removed under the vacuum and the residue was purified by using a Biotage silica gel column chromatography to afford 1.48 g (89.6% yield) of 6-bromo-4-ethylsulfanyl-quinoline as an yellow solid: EI-HRMS m/e calcd for C11H10BrNS (M+) 266.9717, found 266.9715.

Workup

  1. additionAfter addition, it
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined extracts were washed with brine solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration of the drying agent
  6. customthe filtrate was removed under the vacuum
  7. customthe residue was purified

Sources & evidence

ORD record
ord-e57c0c3d800645768b3099c9b90633b7
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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