Ethanol → 2-(5-Methyl-4-imidazolylmethylthio)ethanol

HRID 1112224Notes

Reaction equation

HRID 1112224 reaction equation
[Na].[SH:2]C(O)C.Cl.[CH3:7][C:8]1[N:9]=[CH:10][NH:11][C:12]=1[CH2:13]Cl.[CH2:15]([OH:17])[CH3:16]>>[CH3:7][C:8]1[NH:9][CH:10]=[N:11][C:12]=1[CH2:13][S:2][CH2:16][CH2:15][OH:17]

Participants

5

Reactant 4

HCID 702EthanolHCID 4713212Mercapto-ethanolHCID 5360545Sodium2×HCID 178433265HCID 178433265, compound

Product 1

HCID 127972732-(5-Methyl-4-imidazolylmethylthio)ethanol

Procedure

Sodium (3.0 g) was added, with stirring under nitrogen, to dry ethanol (75 ml). After the sodium had dissolved mercaptoethanol (9.0 ml) was introduced and to this mixture was added 4-methyl-5-chloromethylimidazole hydrochloride (10 g), as a solid, over a period of 1.5 hours at room temperature. The mixture was then stirred for a further 1 hour at room temperature. After this time the reaction was warmed and the ethanol distilled off at reduced pressure. The residue was taken up in water, acidified with concentrated hydrochloric acid, and continuously extracted with ether to remove the excess mercaptoethanol. The aqueous fraction was then basified using solid sodium carbonate and continuously extracted with ethyl acetate. To the extract was added a further volume of ethyl acetate and the whole warmed to re-dissolve the crude product which had deposited. After drying (MgSO4) and reducing the volume, crystallisation from this solution below 40° and cooling to -15° afforded 2-(5-methyl-4-imidazolylmethylthio)ethanol, m.p. 74°-76°.

Workup

  1. additionwas introduced and to this mixture
  2. temperatureAfter this time the reaction was warmed
  3. distillationthe ethanol distilled off at reduced pressure
  4. extractioncontinuously extracted with ether
  5. customto remove the excess mercaptoethanol
  6. extractioncontinuously extracted with ethyl acetate
  7. additionTo the extract was added a further volume of ethyl acetate
  8. temperaturethe whole warmed
  9. dissolutionto re-dissolve the crude product which
  10. dry with materialAfter drying (MgSO4)
  11. customthe volume, crystallisation from this solution below 40°
  12. temperaturecooling to -15°

Sources & evidence

ORD record
ord-7d4b8525475843258dedbbdaebeea0d6
Source dataset
uspto-grants-1978_10
Patent number
US04120972

Reaction notes

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