Potassium Carbonate → Azoxystrobin

HRID 1859228Notes

Reaction equation

HRID 1859228 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>CO>[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 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-cyanophenol (12.6 g), potassium carbonate (8.28 g) and (E)-methyl 2-[2-(6-chloropyrimidin4-yloxy)phenyl]-3-methoxypropenoate (33.0 g) was heated at 120° C. for 3 hours. The mixture was then cooled to 100° C. after which methanol (40 ml) was added to help cooling to 65° C. The resulting mixture was cooled to 0-5° C. and kept at this temperature for 1 hour. The mixture was filtered to leave (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate as the residue (87.5%

Workup

  1. additionwas added
  2. temperatureto help cooling to 65° C
  3. temperatureThe resulting mixture was cooled to 0-5° C.
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-dc263c41d6084113936df31f0ac54159
Source dataset
uspto-grants-2000_11
Patent number
US06153750

Reaction notes

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