Methyl Methanesulfonate → 1-(2-Hydroxyethyl)-2-methylthioimidazoline mesylate

HRID 256541

Reaction equation

HRID 256541 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][C:7](=S)[N:6]=[CH:5]1.[CH3:10][S:11]([O:14]C)(=[O:13])=[O:12]>C(O)C.COC(C)(C)C>[S:11]([OH:14])(=[O:13])(=[O:12])[CH3:10].[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][N:6]=[C:5]1[S:11][CH3:10]

Participants

5

Reactant 2

HCID 4156Methyl MethanesulfonateHCID 197853781-(2-Hydroxyethyl)-2-imidazolinethione

Product 1

HCID 197853791-(2-Hydroxyethyl)-2-methylthioimidazoline mesylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Twenty grams of 1-(2-hydroxyethyl)-2-imidazolinethione and methyl methanesulfonate (12.75 ml) are dissolved in ethyl alcohol (90 mL) and refluxed for 2 hours. The mixture is cooled to room temperature and diluted with t-butyl methyl ether (1 liter). An oil separates which solidifies on keeping the mixture in the freezer at -20° C. for a few days. The solid is then filtered, washed with butyl methyl ether and dried to give 1-(2-hydroxyethyl)-2-methylthioimidazoline mesylate, melting point 78.9°-81.5° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. customat -20° C.
  3. customfor a few days
  4. filtrationThe solid is then filtered
  5. washwashed with butyl methyl ether
  6. customdried

Sources & evidence

ORD record
ord-0ed87c03565f4cb18279d3a096d2c6be
Source dataset
uspto-grants-1993_11
Patent number
US05258381

Linked notes

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