Hydrazine → 1-(2-Hydroxyethyl)-2-hydrazinoimidazoline mesylate

HRID 256542

Reaction equation

HRID 256542 reaction equation
[S:1]([OH:5])(=[O:4])(=[O:3])[CH3:2].[OH:6][CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][N:11]=[C:10]1SC.[NH2:16][NH2:17]>C(O)C.COC(C)(C)C>[S:1]([OH:5])(=[O:4])(=[O:3])[CH3:2].[OH:6][CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][N:11]=[C:10]1[NH:16][NH2:17]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 197853791-(2-Hydroxyethyl)-2-methylthioimidazoline mesylate

Product 1

HCID 197854081-(2-Hydroxyethyl)-2-hydrazinoimidazoline mesylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

1-(2-Hydroxyethyl)-2-methylthioimidazoline mesylate (35 g, 0.136 mole) is suspended in ethyl alcohol (80 ml) and treated with anhydrous hydrazine (9.3 ml, 0.296 mole). The mixture became clear immediately. The solution is stirred at room temperature overnight and then diluted with t-butyl methyl ether (1 liter). On storage of the mixture in the freezer at -20° C., crystals separated, which are filtered, washed well with t-butyl methyl ether and dried. Recrystallization from isopropyl alcohol and t-butyl methyl ether gives 1-(2-hydroxyethyl)-2-hydrazinoimidazoline mesylate, melting point 85°-88° C.

Workup

  1. customOn storage of the mixture in the freezer at -20° C., crystals separated
  2. filtrationwhich are filtered
  3. washwashed well with t-butyl methyl ether
  4. customdried
  5. customRecrystallization from isopropyl alcohol and t-butyl methyl ether

Sources & evidence

ORD record
ord-c9809d95a10348d3ab8f28f924a495e8
Source dataset
uspto-grants-1993_11
Patent number
US05258381

Linked notes

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