m-Chloroperbenzoic acid → HCID 20028995, Verbindung

HRID 1722566

Reaktionsgleichung

Reaktionsgleichung von HRID 1722566
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[C:9]([NH:12][CH2:13][CH2:14][Cl:15])(=[O:11])[CH3:10].ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl-:15].[C:9]([NH:12][CH2:13][CH2:14][N+:6]1[CH:7]=[CH:8][C:3]([S:2]([CH3:1])=[O:24])=[CH:4][CH:5]=1)(=[O:11])[CH3:10]

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 81815N-(2-Chloroethyl)acetamideHCID 1409384-(Methylthio)pyridine

Produkt 1

HCID 20028995HCID 20028995, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

The starting material may be obtained as follows: Reaction of 4-methylthiopyridine with 4 equivalents of N-acetyl-2-chloroethylamine at 80° for 4 hours gave, after precipitation from CH2Cl2 solution with EtOAc, 1-(2-acetylaminoethyl)-4-methylthipyridinium chloride in solvent B:-1.76(s, 3H); 2.69(s, 3H); 3.6(t, 2H); 4.5(t, 2H); 7.87(d, 2H); 8.64(d, 2H). This compound was reacted with one equivalent of metachlorperbenzoic acid in CH2Cl2 /TFA at 0° to ambient temperature for 30 minutes. The product was precipitated from CH2Cl2 /MeOH solution with ether to give 1-(2-acetylaminoethyl)-4-methanesulphinylpyridinium chloride. n.m.r. in solvent B:-1.76(s, 3H); 3.0(s, 3H); 3.66(t, 2H); 4.74(t, 2H); 8.47(d, 2H); 9.22(d, 2H).

Aufarbeitung

  1. customThe starting material may be obtained
  2. customgave
  3. customafter precipitation from CH2Cl2 solution with EtOAc, 1-(2-acetylaminoethyl)-4-methylthipyridinium chloride in solvent B
  4. customThe product was precipitated from CH2Cl2 /MeOH solution with ether

Quellen und Nachweise

ORD-Eintrag
ord-aa7cd582bb074d63ae857061f4c38f83
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04855420

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