HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl orthoformate → Ethyl (3,5-dichloropyridazin-4-yl)imidoformate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl orthoformate | HCID 31214 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | 3,5-Dichloro-1,4-dihydropyridazin-4-imine | HCID 6403201 | — |
| Product | Ethyl (3,5-dichloropyridazin-4-yl)imidoformate | HCID 86723250 | 60% |
Reaction Steps
To a stirred suspension of 3,5-dichloro-4-aminopyridazine (5 g, 31 mmol) in triethyl orthoformate (205 mL) was added pyridinium para-toluenesulfonate (387 mg, 1.5 mmol) and the resultant solution was heated at 100° C. for 16 hours. The reaction mixture was cooled to room temperature then evaporated in vacuo and the crude residue was purified by silica gel column chromatography eluting with hexane:EtOAc (80:20) to afford the title compound as a light brown oil in 60% yield, 4 g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08952008B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-86ad46f5e07143a6b5022896ce376654 |
| Source note | uspto-grants-2015_02 |