Thionyl Chloride → 2-(2-Chloroethylthio)-1-methylimidazole hydrochloride

HRID 279615Notes

Reaction equation

HRID 279615 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][S:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1>ClC(Cl)Cl>[ClH:3].[Cl:3][CH2:6][CH2:7][S:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27748452-[(1-methyl-1H-imidazol-2-yl)thio]ethan-1-ol

Product 1

HCID 226249432-(2-Chloroethylthio)-1-methylimidazole hydrochlorideYield 77%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

Thionyl chloride (1.41 ml, 19 mmol) was slowly added to a solution of 2-(2-hydroxyethylthio)-1-methylimidazole (1.81 g, 11 mmol) in trichloromethane (20 ml) at 5° C. The mixture was stirred for 1 hour at 5° C. and then for 3 hours at ambient temperature. The volatiles were removed by evaporation and the residue azeotroped with toluene to give 2-(2-chloroethylthio)-1-methylimidazole hydrochloride (1.5 g, 77%). 1H NMR Spectrum: (DMSOd6) 3.58 (t, 2H); 3.78(s, 3H); 3.80(t, 2H); 7.78(d, 1H); 7.83(d, 1H)

Workup

  1. waitfor 3 hours at ambient temperature
  2. customThe volatiles were removed by evaporation
  3. customthe residue azeotroped with toluene

Sources & evidence

ORD record
ord-aca57a7fafd048569913b29bcba37467
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

Loading…