2-Chloroethanol → 2-[(1-methyl-1H-imidazol-2-yl)thio]ethan-1-ol

HRID 1384628Notes

Reaction equation

HRID 1384628 reaction equation
Cl[CH2:2][CH2:3][OH:4].[SH:5][C:6]1[N:7]([CH3:11])[CH:8]=[CH:9][N:10]=1>[OH-].[Na+]>[OH:4][CH2:3][CH2:2][S:5][C:6]1[N:7]([CH3:11])[CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 342-ChloroethanolHCID 178480602HCID 178480602, compound

Product 1

HCID 27748452-[(1-methyl-1H-imidazol-2-yl)thio]ethan-1-olYield 82.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloroethanol (3 g, 37 mmol) was added to a solution of 2-mercapto-1-methylimidazole (3.45 g, 30 mmol) in 2M aqueous sodium hydroxide solution (30 ml) and the mixture heated at 100° C. for 2 hours. The mixture was allowed to cool and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and the solvent removed by evaporation to give 2-(2-hydroxyethylthio)-1-methylimidazole (3.9 g, 82%). 1H NMR Spectrum: (DMSOd6) 3.04(t, 2H); 3.30(s, 3H); 3.54(t, 2H); 5.00(s, 1H); 6.87(s, 1H); 7.20(s, 1H)

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-ee8cccb3e1e84cc098673571127cec83
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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