m-Chloroperbenzoic acid → 1-(2-Acetylaminoethyl)-4-methanesulphinylpyridinium chloride

Participants

Reaction Steps

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).

Provenance & Evidence