Methylamine → HCID 178485068, compound

HRID 1702480Notes

Reaction equation

HRID 1702480 reaction equation
[C:1]([NH:3][C:4]([N:6](C#N)[CH2:7][CH2:8][S:9][CH2:10][C:11]1[N:12]=[CH:13][NH:14][C:15]=1[CH3:16])=[NH:5])#[N:2].[CH3:19]N>C(O)C>[C:1]([N:3]=[C:4]([NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[N:12]=[CH:13][NH:14][C:15]=1[CH3:16])[NH:5][CH3:19])#[N:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 178433682HCID 178433682, compound

Product 1

HCID 178485068HCID 178485068, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N,N'-Dicyano-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine (527 mg) was added to a solution of CH3NH2 in ethanol (40%, 3.1 g) and stirred for 47 hrs. at room temperature. After concentration under a reduced pressure, the residue was triturated with CH3CN. The insuluble starting material was filtered off and the filtrate was concentrated under a reduced pressure and chromatographed on SiO2 [eluant: CH3CN-CH3OH (4:1)]. The resulting crude product was purified by preparative thin layer chromatography [SiO2, CH3 --COOC2H5 --CH3OH-- 28% NH3 (aq) (10:1:1)] and recrystallized from CH3CN to give N"-cyano-N-methyl-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine (1.0 mg). m.p. 135°-137° C.

Workup

  1. customat room temperature
  2. concentrationAfter concentration under a reduced pressure
  3. customthe residue was triturated with CH3CN
  4. filtrationwas filtered off
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. customchromatographed on SiO2 [eluant: CH3CN-CH3OH (4:1)]
  7. customThe resulting crude product was purified by preparative thin layer chromatography [SiO2, CH3 --COOC2H5 --CH3OH-- 28% NH3 (aq) (10:1:1)]
  8. customrecrystallized from CH3CN

Sources & evidence

ORD record
ord-a92e5ae1f78344358677343320a8241b
Source dataset
uspto-grants-1983_04
Patent number
US04381395

Reaction notes

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