m-Chloroperbenzoic acid → Hydrochloric Acid

HRID 2286222Notes

Reaction equation

HRID 2286222 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:6]=[CH:7][C:8]=1[Cl:9].[Cl:18]C1C=C(C=CC=1)C(OO)=[O:23]>C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[C:5]([S:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:23])[CH:6]=[CH:7][C:8]=1[Cl:9].[ClH:18]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 127602202-{[(3,4-Dichlorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)

Product 2

HCID 313Hydrochloric AcidYield 252.3%HCID 127602292-[(3,4-Dichlorobenzene-1-sulfinyl)methyl]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 2-(((3,4-dichlorophenyl)thio)methyl)pyridine, hydrochloride (2.0 g) in methylene chloride (50 ml) at 0° C. was treated with a solution of m-chloroperoxybenzoic acid (1.5 g) in methylene chloride (25 ml). The mixture was allowed to warm to ambient temperature and was stirred for 5 hours. The solution was washed with saturated sodium carbonate solution and water, then dried (MgSO4). The residue was dissolved in acetone and converted into the hydrochloride with ethereal HCl. N.m.r. showed approximately 35% of starting material remaining so the material was suspended in methylene chloride (50 ml) and treated with further m-chloroperoxybenzoic acid (2×500 g). The solution was washed with saturated sodium carbonate solution and water, dried (MgSO4), evaporated and the residue was dissolved in acetone and the hydrochloride precipitated with ethereal HCl solution. Recrystallisation from propan-2-ol/ether gave the title compound, hydrochloride (0.6 g) mp 178° C. decomp (Found: C44.7; H,3.2; N,4.2. C12H9Cl2NOS.HCl requires C,44.7; H,3.1; N,4.3%).

Workup

  1. washThe solution was washed with saturated sodium carbonate solution and water
  2. dry with materialdried (MgSO4)
  3. dissolutionThe residue was dissolved in acetone
  4. additiontreated with further m-chloroperoxybenzoic acid (2×500 g)
  5. washThe solution was washed with saturated sodium carbonate solution and water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. dissolutionthe residue was dissolved in acetone
  9. customthe hydrochloride precipitated with ethereal HCl solution
  10. customRecrystallisation from propan-2-ol/ether

Sources & evidence

ORD record
ord-09606a99d93b466aa01d93840a22f160
Source dataset
uspto-grants-1982_04
Patent number
US04327102

Reaction notes

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