m-Chloroperbenzoic acid → Hydrochloric Acid

HRID 1074931Notes

Reaction equation

HRID 1074931 reaction equation
Cl.[F:2][C:3]([F:19])([F:18])[C:4]1[CH:5]=[C:6]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:7]=[CH:8][CH:9]=1.[Cl:20]C1C=C(C=CC=1)C(OO)=[O:25]>C(Cl)Cl>[F:19][C:3]([F:2])([F:18])[C:4]1[CH:5]=[C:6]([S:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:25])[CH:7]=[CH:8][CH:9]=1.[ClH:20]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 129532902-({[3-(Trifluoromethyl)phenyl]sulfanyl}methyl)pyridine--hydrogen chloride (1/1)

Product 2

HCID 313Hydrochloric AcidYield 419.3%HCID 127602352-{[3-(Trifluoromethyl)benzene-1-sulfinyl]methyl}pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 2-(((3-trifluoromethylphenyl)thio)methylpyridine, hydrochloride (2.0 g) in methylene chloride (50 ml) at 0° C. was treated portionwise with m-chloroperoxybenzoic acid (1.5 g) over 1/2 hour. The mixture was allowed to warm to ambient temperature and the mixture was stirred a further 1/2 hour. The solution was washed with saturated Na2CO3 solution and water, dried (MgSO4) and evaporated. The residue was converted into the hydrochloride, in acetone with ethereal HCl solution, which was recrystallised from acetone-ether to give the title compound, hydrochloride (1.0 g) mp 135°-6° C. (Found: C,48.3; H,3.7; N,4.0 C13H10F3NOS.HCl requires C,48.4; H,3.45; N,4.35%).

Workup

  1. washThe solution was washed with saturated Na2CO3 solution and water
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customwas recrystallised from acetone-ether

Sources & evidence

ORD record
ord-d05d22edf9d648a6a8262aa293f52237
Source dataset
uspto-grants-1983_07
Patent number
US04394509

Reaction notes

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