Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl Isobutyl Ketone | HCID 7909 | — |
| Reactant | Dabco | HCID 9237 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate | HCID 11782200 | — |
| Solvent | Water | HCID 962 | — |
| Product | Azoxystrobin | HCID 3034285 | 97.2% |
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 (214 g), and heated to 45-50° C. 2-cyanophenyl (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 at this temperature for 4.5 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 97.2% 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-c00619b0959b4581be75fdba65f25472 |
|---|
| Source note | uspto-grants-2012_02 |
|---|
