Pyridine → HCID 88620974, compound

HRID 231951Notes

Reaction equation

HRID 231951 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].[F:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.N1C=CC=CC=1>C(#N)C>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([S:21][C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 677894-FluorothiophenolHCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 88620974HCID 88620974, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 4-acetoxybenzoyl chloride (7.74 g) in dry acetonitrile (10 ml) was added to a solution of 4-fluorothiophenol (5.00 g) in acetonitrile (40 ml). The mixture was cooled to 5° C. by immersion in an ice-water bath and pyridine (3.15 ml) added dropwise to the stirred solution. The mixture was stirred at 5° C. for 1 hour, allowed to reach room temperature and stirred for a further 2 hours, and then the solvents were evaporated in vacuo. The residue was partitioned between ethyl acetate and water and the separated organic layer was washed successively with water, dilute hydrochloric acid, and water again. Evaporation of the solution, which had been dried over magnesium sulphate, afforded the desired thioester as a pale yellow solid (10.81 g).

Workup

  1. customto reach room temperature
  2. stirringstirred for a further 2 hours
  3. customthe solvents were evaporated in vacuo
  4. customThe residue was partitioned between ethyl acetate and water
  5. washthe separated organic layer was washed successively with water, dilute hydrochloric acid, and water again
  6. customEvaporation of the solution, which
  7. dry with materialhad been dried over magnesium sulphate

Sources & evidence

ORD record
ord-d924ae4f4a5d45699f9e0e98702e2a51
Source dataset
uspto-grants-1989_07
Patent number
US04849419

Reaction notes

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