Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dabco | HCID 9237 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Hydroxybenzonitrile | HCID 11907 | — |
| Reactant | Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate | HCID 11782200 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Methyl Isobutyl Ketone | HCID 7909 | — |
| Product | Azoxystrobin | HCID 3034285 | 91.8% |
Reaction Steps
Methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (98.4 g at 97.7% strength; prepared as described in WO 92/08703) was added to MIBK (210 g) and water (38.3 g) and heated to 45-50° C. 2-Cyanophenol (40.1 g), potassium carbonate (63.4 g) and DABCO (0.51 g) were added and the temperature was raised to 80° C. and held for 5.5 hours. Water (316 g) was added and agitation continued for 30 minutes before settling and separating the aqueous layer. Analysis of the MIBK solution revealed a 91.8% yield of methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (azoxystrobin).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08124761B2 |
|---|
| Source dataset | uspto-grants-2012_02 |
|---|
| ORD ID | ord-b5cdd34b6a204670a48e6bbc6c3770e9 |
|---|
| Source note | uspto-grants-2012_02 |
|---|
