Acetyl chloride → N-{4-[(4-fluorophenyl)sulfanyl]phenyl}acetamide

HRID 371515

Reaction equation

HRID 371515 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:23](=[O:25])[CH3:24])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 27747404-[(4-Fluorophenyl)sulfanyl]aniline

Product 1

HCID 1486273N-{4-[(4-fluorophenyl)sulfanyl]phenyl}acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 2.19 g portion of this amine was dissolved in 50 ml of dichloromethane, cooled in an ice bath and treated with 1.52 g of triethylamine. The mixture was then treated dropwise with a solution of 1.18 g of acetyl chloride in 20 ml of dichloromethane over 20 minutes. This mixture was stirred at room temperature overnight, then the solution was washed successively with water, saturated aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, filtered and concentrated to dryness. The residue was recrystallized from methanol-water, giving 2.26 g of the desired product as colorless crystals, mp 140°-141° C.

Workup

  1. temperaturecooled in an ice bath
  2. washthe solution was washed successively with water, saturated aqueous sodium bicarbonate, water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was recrystallized from methanol-water

Sources & evidence

ORD record
ord-c8aa9d73a50f496f9dc880b3e551b0e3
Source dataset
uspto-grants-1985_07
Patent number
US04532349

Linked notes

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