4-(Methylthio)pyridine → HCID 20193882, compound

HRID 2118591Notes

Reaction equation

HRID 2118591 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.Cl.[CH3:10][N:11]([CH3:15])[CH2:12][CH2:13][Cl:14]>CCO>[Cl-:14].[CH3:10][N:11]([CH3:15])[CH2:12][CH2:13][N+:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 1409384-(Methylthio)pyridineHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 20193882HCID 20193882, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material may be obtained as follows: Reaction of 4-methylthiopyridine with one equivalent of 2-dimethylaminoethyl chloride hydrochloride in EtOH at reflux for 18 hours gave 1-(2-dimethylaminoethyl)-4-methylthiopyridinium chloride. n.m.r. in solvent B: 2.7(s, 3H); 2.87(s, 6H); 3.75(t, 2H); 4.92(t, 2H); 7.98(d, 2H); 8.84(d, 2H). Oxidation of this compound with metachlorperbenzoic acid in CH2Cl2 /TFA at 0° to ambient temperature for 40 minutes gave 1-(2-dimethylaminoethyl)-4-methanesulphinylpyridinium chloride. n.m.r. in solvent B: 3.0(s, 6H); 3.34(s, 3H); 3.87(t, 2H); 5.16(t, 2H); 8.52(d, 2H); 9.36(d, 2H).

Workup

  1. customThe starting material may be obtained
  2. temperatureat reflux for 18 hours

Sources & evidence

ORD record
ord-ffb3853476fc4d8cb5f5dd959782405e
Source dataset
uspto-grants-1987_07
Patent number
US04678781

Reaction notes

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