Pyridine → 4-{[(2,4,5-Trichlorophenyl)sulfanyl]carbonyl}phenyl acetate

HRID 231948Notes

Reaction equation

HRID 231948 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].[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([Cl:22])=[CH:17][C:16]=1[SH:23].N1C=CC=CC=1.C(OCC)(=O)C>C(#N)C>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([S:23][C:16]2[CH:17]=[C:18]([Cl:22])[C:19]([Cl:21])=[CH:20][C:15]=2[Cl:14])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 195972,4,5-TrichlorobenzenethiolHCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 713332164-{[(2,4,5-Trichlorophenyl)sulfanyl]carbonyl}phenyl acetateYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 4-acetoxybenzoyl chloride (8.37 g) in dry acetonitrile (20 ml) was added to a solution of 2,4,5-trichlorothiophenol (9.00 g) in dry acetonitrile (120 ml) and the mixture stirred at room temperature whilst pyridine (3.41 ml) was added dropwise over 10 minutes. Stirring was continued until the reaction was complete, when ethyl acetate was added and the solution washed with water. Evaporation of the solution, which had been dried over magnesium sulphate, afforded the desired thioester (15.36 g).

Workup

  1. additionwas added dropwise over 10 minutes
  2. washthe solution washed with water
  3. customEvaporation of the solution, which
  4. dry with materialhad been dried over magnesium sulphate

Sources & evidence

ORD record
ord-fd73157b07b94d0194c274f0aa2c0646
Source dataset
uspto-grants-1989_07
Patent number
US04849419

Reaction notes

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