Thionyl Chloride → 1-Chloro-2(5-methyl-4-imidazolylmethylthio)ethane hydrochloride

HRID 46485Notes

Reaction equation

HRID 46485 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10]O.S(Cl)([Cl:14])=O>C(Cl)(Cl)Cl>[ClH:14].[Cl:14][CH2:10][CH2:9][S:8][CH2:7][C:3]1[N:4]=[CH:5][NH:6][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 127972732-(5-Methyl-4-imidazolylmethylthio)ethanol

Product 1

HCID 132173611-Chloro-2(5-methyl-4-imidazolylmethylthio)ethane hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(5-Methyl-4-imidazolylmethylthio)ethanol (0.34 g, 2 mmol) and thionyl chloride (0.238 g, 2 mmol) were heated together, with stirring, at reflux temperature in chloroform (10 ml) for one hour, giving a grey solution and a green oil. A second equivalent of thionyl chloride (0.238 g) was added at reflux temperature and immediately the oil went into solution and a solid started to crystallise. After a further 15 minutes at reflux temperature the mixture was cooled and the solid collected (0.395 g). Recrystallisation from acetonitrile gave 1-chloro-2-(5-methyl-4-imidazolylmethylthio)ethane hydrochloride, m.p. 163°-165°, (0.29 g).

Workup

  1. customgiving a grey solution
  2. temperatureat reflux temperature
  3. customto crystallise
  4. temperatureAfter a further 15 minutes at reflux temperature the mixture
  5. temperaturewas cooled
  6. customthe solid collected (0.395 g)
  7. customRecrystallisation from acetonitrile

Sources & evidence

ORD record
ord-a1e320da4d2e46de8534e2d83a32dff2
Source dataset
uspto-grants-1979_11
Patent number
US04173644

Reaction notes

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