4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → HCID 178485068, compound

HRID 1702478Notes

Reaction equation

HRID 1702478 reaction equation
[C:1]([N:3]=[C:4]([NH:9][CH3:10])S(O)(=O)=O)#[N:2].[CH3:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH2:17][S:18][CH2:19][CH2:20][NH2:21]>C(O)C>[C:1]([N:3]=[C:4]([NH:21][CH2:20][CH2:19][S:18][CH2:17][C:13]1[N:14]=[CH:15][NH:16][C:12]=1[CH3:11])[NH:9][CH3:10])#[N:2]

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 178485083HCID 178485083, compound

Product 1

HCID 178485068HCID 178485068, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of cyanoimino-methylaminomethanesulfonic acid (DBU salt) (0.70 g) and 2-(5-methylimidazol-4-ylmethylthio)ethylamine (0.57 g) in ethanol (14 ml) was heated under reflux for 7 hrs. After removal of the solvent under a reduced pressure, the residue was purified by column chromatography on SiO2 [eluant: CH3CN-CH3OH (4:1)]. After concentration of the eluate under a reduced pressure, the residue was subjected to preparative thin layer chromatography [SiO2, CH3COOCH3 -CH3OH- 28% NH3 (aq) (10:1:1)] and then recrystallized from CH3OH-CH3CN to give N"-cyano-N-methyl-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine (0.18 g). Yield 32.4%, m.p. 140°-141° C.

Workup

  1. temperatureunder reflux for 7 hrs
  2. customAfter removal of the solvent under a reduced pressure
  3. customthe residue was purified by column chromatography on SiO2 [eluant: CH3CN-CH3OH (4:1)]
  4. customrecrystallized from CH3OH-CH3CN

Sources & evidence

ORD record
ord-37fbb9b28bf7477491f6c74f65d7283e
Source dataset
uspto-grants-1983_04
Patent number
US04381395

Reaction notes

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