Triethylamine → HCID 14932139, compound

HRID 1490345Notes

Reaction equation

HRID 1490345 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[SH:12].C(N(CC)CC)C>C(Cl)Cl>[C:1]([S:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][N:6]=1)(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 178418616HCID 178418616, compound

Product 1

HCID 14932139HCID 14932139, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15.6 ml (1.2 equivalents) of propionyl chloride were slowly added at room temperature to a solution of 20 g of 2-pyridinethiol and 25.1 ml (1.2 equivalents) of triethylamine in 200 ml of anhydrous methylene chloride, and the resulting mixture was stirred for 1 hour. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was mixed with ethyl acetate. The organic solution thus obtained was washed twice with a dilute aqueous solution of sodium hydrogencarbonate and then with water. The organic layer was separated and then dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was subjected to fractional distillation in vacuo, to give 27 g (yield 90%) of the title compound, boiling at 93° C./0.05 mmHg (6.7 Pa).

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. customThe organic solution thus obtained
  4. washwas washed twice with a dilute aqueous solution of sodium hydrogencarbonate
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customafter which the solvent was removed by distillation under reduced pressure
  8. distillationThe residue was subjected to fractional distillation in vacuo

Sources & evidence

ORD record
ord-0dbd57d424db48aa824487c4e12d2297
Source dataset
uspto-grants-1997_10
Patent number
US05681951

Reaction notes

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