Potassium Carbonate → Azoxystrobin

HRID 1859233Notes

Reaction equation

HRID 1859233 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+].CN1CCCC1=O.Cl[C:24]1[N:29]=[CH:28][N:27]=[C:26]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2/[C:37](=[CH:42]\[O:43][CH3:44])/[C:38]([O:40][CH3:41])=[O:39])[CH:25]=1>C1(C)C=CC=CC=1.O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][C:24]1[N:29]=[CH:28][N:27]=[C:26]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2/[C:37](=[CH:42]\[O:43][CH3:44])/[C:38]([O:40][CH3:41])=[O:39])[CH:25]=1)#[N:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 119072-HydroxybenzonitrileHCID 13387N-methyl-2-pyrrolidoneHCID 11782200Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate

Product 1

HCID 3034285Azoxystrobin

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 2-cyanophenol (13.2 g), potassium carbonate (20.7 g), N-methyl-2-pyrrolidinone (15.0 g), (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (32.8 g) and water (35 g) was heated at 105° C. for 15 hours. Any distillates were allowed to come off under atmospheric conditions. The reaction mixture was mixed with toluene. The organic layer was then separated. Toluene and N-methyl-2-pyrrolidinone were removed from the organic phase by vacuum distillation (110° C., 20 mmHg). The melt was cooled to 90° C. after which methanol (40 ml) was added to help cooling to 65-75° C. The resulting mixture was cooled to ambient and kept at this temperature overnight. It was then further cooled to 0-5° C. and held for another 1 hour period. The mixture was filtered to leave (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate as the residue (68.2% isolated yield).

Workup

  1. customThe organic layer was then separated
  2. customToluene and N-methyl-2-pyrrolidinone were removed from the organic phase by vacuum distillation (110° C., 20 mmHg)
  3. temperatureThe melt was cooled to 90° C. after which methanol (40 ml)
  4. additionwas added
  5. temperatureto help cooling to 65-75° C
  6. temperatureThe resulting mixture was cooled to ambient and
  7. customkept at this temperature overnight
  8. temperatureIt was then further cooled to 0-5° C.
  9. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-10ca038f28f9446fae18e3e428bba112
Source dataset
uspto-grants-2000_11
Patent number
US06153750

Reaction notes

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