Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyanamide | HCID 9864 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole | HCID 665568 | — |
| Reactant | N-methyl-chloroformimidoyl chloride | HCID 12647927 | — |
| Reactant | N'-methyl-N-[2-(5-methylimidazol-4-ylmethylthio)ethyl]chloroformamidine | HCID 20504046 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178485068 | HCID 178485068 | 19% |
Reaction Steps
A solution of N-methyl-chloroformimidoyl chloride (1.12 g), 2-(5-methylimidazol-4-ylmethylthio)ethylamine (0.855 g) and DBU (0.988 g) in CH2Cl2 (16 ml was heated under reflux for 6 hrs. To the reaction mixture containing N'-methyl-N-[2-(5-methylimidazol-4-ylmethylthio)ethyl]chloroformamidine was added a solution of cyanamide (0.84 g) and DBU (3.04 g) in CH2Cl2 (16 ml). After refluxing for 15 hrs., the solvent was removed and the residue was chromatographed [SiO2, CH3CN-CH3OH (4:1)]. The crude product was purified by preparative chromatography [SiO2, CH3COOC2H5 --CH3OH-- 28% NH3 (aq) (10:1:1)] and then recrystallization from CH3CN to give N"-cyano-N-methyl-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine (0.24 g). Yield 19.0%, m.p. 139°-141° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04381395 |
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| Source dataset | uspto-grants-1983_04 |
|---|
| ORD ID | ord-5496a29136d64303aa928b62eb5cb79d |
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| Source note | uspto-grants-1983_04 |
|---|
