Methyl Isobutyl Ketone → Azoxystrobin

HRID 1645234Notes

Reaction equation

HRID 1645234 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])[CH:3]=1.C[CH:24]([CH2:26][C:27]([CH3:29])=[O:28])[CH3:25].[C:30](=O)([O-])[O-].[K+].[K+].C1N2CC[N:38](CC2)[CH2:37]1>O>[C:37]([C:26]1[CH:24]=[CH:25][CH:30]=[CH:29][C:27]=1[O:28][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])[CH:3]=1)#[N:38]

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 9237DabcoHCID 11430Potassium CarbonateHCID 11782200Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate

Product 1

HCID 3034285AzoxystrobinYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
47.5 °C

Procedure

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).

Workup

  1. temperaturethe temperature was raised to 80° C.
  2. waitagitation continued for 30 minutes
  3. customseparating the aqueous layer

Sources & evidence

ORD record
ord-c00619b0959b4581be75fdba65f25472
Source dataset
uspto-grants-2012_02
Patent number
US08124761B2

Reaction notes

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