HuagongsheHuagongshe Chemistry Print Report · For research reference only
Malononitrile → 2-(2-Ethyl-4-(2,2-dicyanovinyl)phenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Malononitrile | HCID 8010 | — |
| Reactant | 2-(2-Ethyl-4-formylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane | HCID 18316048 | — |
| Catalyst | Piperidine | HCID 8082 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 2-(2-Ethyl-4-(2,2-dicyanovinyl)phenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane | HCID 18316229 | 28.5% |
Reaction Steps
To a solution of 2-(2-ethyl-4-formylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane (Method D11a; 0.037 g, 0.104 mmol) in EtOH (10 mL) was added malononitrile (0.007 g, 0.104 mmol) and piperidine (4 drops). The reaction mixture was stirred at room temp. for 2 h, then concentrated under reduced pressure. The residue was purified by preparative TLC (20% EtOAc/hex) to give 2-(2-ethyl-4-(2,2-dicyanovinyl)phenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane as a yellow solid (0.012 g, 28%): mp 135-136° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06353006B1 |
| Source dataset | uspto-grants-2002_03 |
| ORD ID | ord-2769b1f1397c4dda9629e5d034c637db |
| Source note | uspto-grants-2002_03 |