Pyridine → HCID 57144400, compound

HRID 231949Notes

Reaction equation

HRID 231949 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[C:20]([SH:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=1[F:25].N1C=CC=CC=1>ClCCl>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([S:21][C:20]2[C:19]([F:22])=[C:18]([F:23])[C:17]([F:24])=[C:16]([F:25])[C:15]=2[F:14])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13042Benzenethiol, pentafluoro-HCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 57144400HCID 57144400, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-acetoxybenzoyl chloride (4.96 g) in dry dichloromethane (20 ml) was added dropwise over 15 minutes to a stirred solution of pentafluorothiophenol (5.00 g), pyridine (2.1 ml) and 4-N,N-dimethylaminopyridine (50 mg) in dry dichloromethane (75 ml), the mixture being maintained close to 5° C. by immersion in an ice-bath. The reactants were allowed to reach room temperature overnight and the organic solution was washed successively with aqueous 2M hydrochloric acid, a saturated sodium bicarbonate solution and water. Evaporation of the solution, which had been dried over magnesium sulphate, afforded the desired thioester (8.79 g).

Workup

  1. temperaturethe mixture being maintained
  2. customclose to 5° C. by immersion in an ice-bath
  3. washthe organic solution was washed successively with aqueous 2M hydrochloric acid
  4. customEvaporation of the solution, which
  5. dry with materialhad been dried over magnesium sulphate

Sources & evidence

ORD record
ord-abe5f03dfb0345ff867c47b47215dac3
Source dataset
uspto-grants-1989_07
Patent number
US04849419

Reaction notes

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