Pyridine → HCID 86204449, compound

HRID 378173Notes

Reaction equation

HRID 378173 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1.[Cl:25]CCl>>[C:1]([S:18][C:12]1[CH:17]=[CH:16][C:15]([Cl:25])=[CH:14][CH:13]=1)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344Dichloromethane2×HCID 7969ThiophenolHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 86204449HCID 86204449, compoundYield 96%

Procedure

A solution of cinnamoyl chloride (26.0 g, 156.3 mmol) in dichloromethane (100 mL) was added to a solution of thiophenol (22.6 g, 156.3 mmol) and pyridine (12.6 mL) in dichloromethane (200 mL) in an ice-water bath. After 18 hours at room temperature, the reaction mixture was washed with dilute hydrochloric acid (100 mL, 1N), brine (100 mL), dried (MgSO4) and was concentrated to afford 41.0 g (96%) of the desired thioester as a crystalline solid.

Workup

  1. washthe reaction mixture was washed with dilute hydrochloric acid (100 mL, 1N), brine (100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-cbb339758a3e4bb1a4f202787365a043
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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