m-Chloroperbenzoic acid → HCID 23470801, compound

HRID 127933Notes

Reaction equation

HRID 127933 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH2:14][Cl:15])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:12][CH2:13][CH2:14][Cl:15])=[O:24])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14005891N-{4-[(3-Chloropropyl)sulfanyl]phenyl}acetamide

Product 1

HCID 23470801HCID 23470801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.22 g (0.005 mole) of 3-(p-acetamidophenylthio)propyl chloride in 25 ml of methylene chloride is cooled in an ice bath while 0.88 g (0.005 mole) of m-chloroperbenzoic acid is added in portions. After keeping at room temperature overnight the reaction mixture is washed with excess 0.5 N sodium hydroxide, dried, and concentrated to a light brown oil. By triturating with ether, 1.06 g of 3-(p-acetamidophenylsulfinyl)propyl chloride are obtained. Anal. Calcd for C11H14ClNO2S: C, 50.86; H, 5.45; N, 5.39; Cl, 13.65. Found: C, 50.53; H, 5.59; N, 5.23; Cl, 13.67.

Workup

  1. additionis added in portions
  2. washthe reaction mixture is washed with excess 0.5 N sodium hydroxide
  3. customdried
  4. concentrationconcentrated to a light brown oil
  5. customBy triturating with ether, 1.06 g of 3-(p-acetamidophenylsulfinyl)propyl chloride
  6. customare obtained

Sources & evidence

ORD record
ord-347dc0652ec64c2f84b5a53092b14252
Source dataset
uspto-grants-1981_03
Patent number
US04258045

Reaction notes

Loading…