Sodium Sulfate → HCID 178485068, compound

HRID 1702474Notes

Reaction equation

HRID 1702474 reaction equation
[C:1]([NH:3][C:4]([NH:6][CH3:7])=S)#[N:2].[CH3:8][C:9]1[NH:13][CH:12]=[N:11][C:10]=1[CH2:14][S:15][CH2:16][CH2:17][NH2:18].S([O-])([O-])(=O)=O.[Na+].[Na+]>CC#N>[C:1]([N:3]=[C:4]([NH:18][CH2:17][CH2:16][S:15][CH2:14][C:10]1[N:11]=[CH:12][NH:13][C:9]=1[CH3:8])[NH:6][CH3:7])#[N:2]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 27241251-Cyano-3-methylthiourea

Product 1

HCID 178485068HCID 178485068, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of N-cyano-N'-methylthiourea (DBU salt) (0.534 g), 2-(5-methylimidazol-4-ylmethylthio)ethylamine (1.03 g), HgO (0.868 g) and anhydrous sodium sulfate (2 g) in CH3CN (20 ml) was heated under reflux for 20 hrs. with vigorous stirring. The hot reaction mixture was filtered and the filtrate was dried up and subjected to chromatography on SiO2 [eluant: CH3CN-CH3OH (4:1)]. The resulting crude product was purified by preparative thin layer chromatography [SiO2, AcOEt--MeOH--28% aq. NH3 (10:1:1)] and recrystallized from CH3CN to give N"-cyano-N-methyl-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]-guanidine (38.4 mg). Yield 7.6%, m.p. 136°-138° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hrs
  3. filtrationThe hot reaction mixture was filtered
  4. customthe filtrate was dried up
  5. customThe resulting crude product was purified by preparative thin layer chromatography [SiO2, AcOEt--MeOH--28% aq. NH3 (10:1:1)]
  6. customrecrystallized from CH3CN

Sources & evidence

ORD record
ord-610ef137ae304b709590dc3c90c07b08
Source dataset
uspto-grants-1983_04
Patent number
US04381395

Reaction notes

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