Potassium Carbonate → Azoxystrobin

HRID 1859231Notes

Reaction equation

HRID 1859231 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])#[N:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:17]1[N:22]=[CH:21][N:20]=[C:19]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2/[C:30](=[CH:35]\[O:36][CH3:37])/[C:31]([O:33][CH3:34])=[O:32])[CH:18]=1>O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][C:17]1[N:22]=[CH:21][N:20]=[C:19]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2/[C:30](=[CH:35]\[O:36][CH3:37])/[C:31]([O:33][CH3:34])=[O:32])[CH:18]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119072-HydroxybenzonitrileHCID 11782200Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate

Product 1

HCID 3034285Azoxystrobin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
96 °C

Procedure

A mixture of 2-cyanophenol (13.2 g), potassium carbonate (20.7 g), polyethylene glycol 400 (20.0 g), (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3 -methoxypropenoate (32.8 g) and water (77 g) was heated at 96° C. for 16 hours. The temperature of the solution was then raised to 105° C. and held for a further 12 hours. Any distillates were allowed to come off under atmospheric conditions. (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate was produced (86.6 area %).

Workup

  1. temperatureThe temperature of the solution was then raised to 105° C.

Sources & evidence

ORD record
ord-cd11ed5b2e644a10911914bd3057a871
Source dataset
uspto-grants-2000_11
Patent number
US06153750

Reaction notes

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