HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → N-cyano-N'-[2-(3-isothiazolylmethylthio)ethyl]-N"-methylguanidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | N-Methyl-N'-(2-{[(1,2-thiazol-3-yl)methyl]sulfanyl}ethyl)thiourea | HCID 20466672 | — |
| Reactant | CH2N2Pb | HCID 22262466 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | N-cyano-N'-[2-(3-isothiazolylmethylthio)ethyl]-N"-methylguanidine | HCID 9992541 | — |
Reaction Steps
Lead cyanamide (52.6 g) was added to a solution of N-methyl-N'-[2-(3-isothiazolylmethylthio)ethyl]thiourea (17.7 g) in acetonitrile (500 ml) containing dimethylformamide (50 ml). The mixture was stirred under reflux for 48 hours, then filtered and concentrated. The product was chromatographed on silica gel with ethyl acetate as eluant and recrystallised from isopropyl acetate-ether to give N-cyano-N'-[2-(3-isothiazolylmethylthio)ethyl]-N"-methylguanidine, in a crystalline form, m.p.. 63°-64°. Further recrystallisation from isopropyl acetate afforded the cyanoguanidine in a crystalline form, m.p. 91°-92°.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04000302 |
| Source dataset | uspto-grants-1976_12 |
| ORD ID | ord-f10fa382955b4a959672ebcccb4ed7ec |
| Source note | uspto-grants-1976_12 |