HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanethiol → 5-amino-3-benzylamino-1H-pyrazole-4-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanethiol | HCID 878 | — |
| Reactant | Hydrazine hydrate (1:1) | HCID 24654 | — |
| Reactant | Propanedinitrile, [(methylthio)[(phenylmethyl)amino]methylene]- | HCID 1704435 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 5-amino-3-benzylamino-1H-pyrazole-4-carbonitrile | HCID 10822472 | — |
Reaction Steps
24 ml (0.48 mol) of hydrazine hydrate are added dropwise to a solution of 92 g (0.4 mol) of 3-benzylamino-3-methylsulfanyl-2-cyano-acrylonitrile in 400 ml of methanol, the temperature rising to 40° C. The reaction mixture is slowly heated to boiling (e evolution of MeSH!), boiled for 2 hours, cooled to RT and concentrated by evaporation to a residual volume of ≈200 ml. Dilution with diethyl ether, filtration and washing with diethyl ether yield 5-amino-3-benzylamino-1H-pyrazole-4-carbonitrile [Spectrochimica Acta, 47A, 1635 (1991)]; m.p. 150-152° C.; TLC: Rf=0.41 (ethyl acetate).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06251911B1 |
| Source dataset | uspto-grants-2001_06 |
| ORD ID | ord-cb80dfdd3e074f0f89f6afabafb39d70 |
| Source note | uspto-grants-2001_06 |