m-Chloroperbenzoic acid → HCID 21287983, compound

HRID 868350Notes

Reaction equation

HRID 868350 reaction equation
[Cl:1][CH:2]([CH2:7][C:8]1[CH:9]=[N:10][C:11]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)[C:3]([O:5][CH3:6])=[O:4].ClC1C=CC=C(C(OO)=[O:29])C=1>ClCCl>[Cl:1][CH:2]([CH2:7][C:8]1[CH:9]=[N:10][C:11]([S:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:29])=[CH:12][CH:13]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21287978Methyl α-chloro-6-(phenylthio)-3-pyridinepropanoate

Product 1

HCID 21287983HCID 21287983, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-chloro-3-(6-phenylthio-3-pyridyl)propionate (10.5 g), prepared in substantially the same manner as in Reference Example 5 using the corresponding starting materials, is dissolved in 100 ml of dichloromethane. To the solution, 7.1 g of m-chloroperbenzoic acid is added slowly with stirring under cooling in an ice-water bath. The mixture is stirred at room temperature for 1 hour, washed with saturated sodium carbonate solution, dried over magnesium sulfate, and concentrated to give crude methyl 2-chloro-3-(6-phenylsulfinyl-3-pyridyl)propionate. To the sulfinyl compound is added 170 ml of 4N sodium hydroxide solution, and the mixture is refluxed with stirring for 4 hours. After cooling, the resulting precipitate is collected to give 4.1 g of the title compound.

Workup

  1. temperatureunder cooling in an ice-water bath
  2. stirringThe mixture is stirred at room temperature for 1 hour
  3. washwashed with saturated sodium carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-139d7a0b390a4f8bafc6b3600f623f62
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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