Triethylamine → 2-Propionylthioquinoline

HRID 977636Notes

Reaction equation

HRID 977636 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[SH:16].C(N(CC)CC)C>C(Cl)Cl>[C:1]([S:16][C:7]1[CH:8]=[CH:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]=1)(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 178418736HCID 178418736, compound

Product 1

HCID 196989512-PropionylthioquinolineYield 53.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

480 mg (1.2 equivalents) of propionyl chloride were added, whilst ice-cooling, to a solution of 1 g of 2-quinolinethiol and 0.83 ml (1.2 equivalents) of triethylamine in 20 ml of anhydrous methylene chloride, and the resulting mixture was stirred for 30 minutes. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was mixed with ethyl acetate. This mixture was washed twice with a dilute aqueous solution of sodium hydrogencarbonate and was then washed with water. The organic layer was separated and dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by flash chromatography through silica gel, using a 1:1 by volume mixture of cyclohexane and ethyl acetate as the eluent, to give 600 mg of the title compound having an Rf value of 0.4.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. additionthe resulting residue was mixed with ethyl acetate
  3. washThis mixture was washed twice with a dilute aqueous solution of sodium hydrogencarbonate
  4. washwas then washed with water
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by flash chromatography through silica gel
  9. additionby volume mixture of cyclohexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-76f94fc1c5f0499a8c60189538eed1da
Source dataset
uspto-grants-1997_03
Patent number
US05614624

Reaction notes

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