m-Chloroperbenzoic acid → Hydrochloric Acid

HRID 1074926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1074926
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]

Komponenten

5

Edukt 2

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

Produkt 2

HCID 313Hydrochloric AcidAusbeute 252,3 %HCID 127602292-[(3,4-Dichlorobenzene-1-sulfinyl)methyl]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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 with 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%).

Aufarbeitung

  1. washThe solution with 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

Quellen und Nachweise

ORD-Eintrag
ord-9ce6cfce0cc64e6fb99a7fbc1903c40b
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04394509

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