Pyridine → HCID 88620983, compound

HRID 231950Notes

Reaction equation

HRID 231950 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[C:9]([O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1)(=[O:11])[CH3:10].N1C=CC=CC=1>C(#N)C>[C:9]([O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([S:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:18])=[CH:15][CH:14]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7815p-ChlorothiophenolHCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 88620983HCID 88620983, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-Chlorothiophenol (21.6 g) was dissolved in dry acetonitrile (500 ml) and a solution of 4-acetoxybenzoyl chloride (29.7 g) in acetonitrile (50 ml) was added. The mixture was stirred at room temperature whilst pyridine (12.1 ml) was added rapidly dropwise. When the reaction was complete the bulk of the solvents was removed by evaporation in vacuo and the residue partitioned between ethyl acetate and water. The separated organic layer was washed with water and brine, dried over magnesium sulphate, and evaporated to afford the desired thioester as a pale yellow solid (41.0 g).

Workup

  1. additionwas added rapidly dropwise
  2. customwas removed by evaporation in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe separated organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-9541ebc54bd348ba93bbd8d80320766f
Source dataset
uspto-grants-1989_07
Patent number
US04849419

Reaction notes

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