Pyridine → HCID 88621011, compound

HRID 231952Notes

Reaction equation

HRID 231952 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.N1C=CC=CC=1>C(#N)C>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([S:22][C:19]2[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 127654-MethoxybenzenethiolHCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 88621011HCID 88621011, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 4-acetoxybenzoyl chloride (7.06 g) in dry acetonitrile (15 ml) was added to a solution of 4-methoxythiophenol (5.00 g) in dry acetonitrile (60 ml), and the mixture cooled (ice-bath) and stirred whilst pyridine (2.83 ml) was added dropwise over 10 minutes. The solution was allowed to reach room temperature, stirred for a further 2 hours and the volatile solvents evaporated in vacuo. The residue was partitioned between ethyl acetate and water and the separated organic layer was washed successively with water and brine, dried over magnesium sulphate, and evaporated. Column chromatography of the crude material (silica; ethyl acetate/hexane mixtures as eluant) gave the pure thioester as a pale yellow foam (8.84 g).

Workup

  1. temperaturethe mixture cooled (ice-bath)
  2. additionwas added dropwise over 10 minutes
  3. customto reach room temperature
  4. customthe volatile solvents evaporated in vacuo
  5. customThe residue was partitioned between ethyl acetate and water
  6. washthe separated organic layer was washed successively with water and brine
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-3099fc0be64b4ed4a38e18e046a4a86d
Source dataset
uspto-grants-1989_07
Patent number
US04849419

Reaction notes

Loading…