HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 20273624, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Nitroethane | HCID 6587 | — |
| Reactant | Cyanoacetamide | HCID 7898 | — |
| Reactant | Butylamine | HCID 8007 | — |
| Reactant | Dimethylformamide dimethyl acetal | HCID 78373 | — |
| Reactant | HCID 20273627 | HCID 20273627 | — |
| Reactant | 1-[2-Methoxy-4-(methylsulfanyl)phenyl]propan-2-one | HCID 20273629 | — |
| Reactant | 4-(Dimethylamino)-3-[2-methoxy-4-(methylsulfanyl)phenyl]but-3-en-2-one | HCID 53799811 | — |
| Catalyst | Iron | HCID 23925 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 20273624 | HCID 20273624 | — |
Reaction Steps
The starting material 1,2-dihydro-5-(2-methoxy-4-methylthiophenyl)-6-methyl-2-oxonicotinamide (m.p. 278°-281° [dec.]--from methylene chloride/methanol) is obtained by heating to ebullition 2-methoxy-4-methylthiobenzaldehyde with nitroethane in toluene in the presence of n-butylamine, converting the resultant nitrovinyl compound with iron powder and hydrochloric acid without further characterization to 1-(2-methoxy-4-methylthiophenyl)-2-propanone (b.p. 0.02 mm Hg=140°-150°), heating this compound with N,N-dimethylformamide dimethyl acetal for 3 hours to 80° and reacting the resultant 4-dimethylamino-3-(2-methoxy-4-methylthiophenyl)-3-buten-2-one (m.p. 111°-112°--from ether/petroleum ether) with cyanacetamide in glacial acetic acid at 100°.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04530842 |
| Source dataset | uspto-grants-1985_07 |
| ORD ID | ord-99e14c46b8254096bc7694e865e172f9 |
| Source note | uspto-grants-1985_07 |