m-Chloroperbenzoic acid → Hydrochloric Acid

HRID 1074929Notes

Reaction equation

HRID 1074929 reaction equation
Cl.[F:2][C:3]1[C:8]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[C:7]([F:17])[C:6]([F:18])=[C:5]([F:19])[C:4]=1[F:20].[Cl:21]C1C=C(C=CC=1)C(OO)=[O:26]>C(Cl)Cl>[F:17][C:7]1[C:8]([S:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:26])=[C:3]([F:2])[C:4]([F:20])=[C:5]([F:19])[C:6]=1[F:18].[ClH:21]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 127602242-{[(Pentafluorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)

Product 2

HCID 313Hydrochloric AcidYield 584.2%HCID 127602332-[(2,3,4,5,6-Pentafluorobenzene-1-sulfinyl)methyl]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred suspension of 2-(((pentafluorophenyl)thio)methyl)pyridine, hydrochloride (2.0 g) in methylene chloride (50 ml) at 0° C. was treated portionwise with m-chloroperoxybenzoic acid (1.41 g) over 1/2 hour. The mixture was allowed to warm to ambient temperature, sufficient methylene chloride was added to form a solution, 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 to give the title compound, hydrochloride (1.3 g) mp 154°-6° C. (Found: C,41.6; H,2.15; N,3.8 C12H6F5NOS.HCl requires C41.9; H,2.05; N,4.1%).

Workup

  1. customto form a solution
  2. washThe solution was washed with saturated Na2CO3 solution and water
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-2de23493f3bc4819afde4f6cf29ef202
Source dataset
uspto-grants-1983_07
Patent number
US04394509

Reaction notes

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