Sodium Carbonate → Epyrifenacil

HRID 1862297Notes

Reaction equation

HRID 1862297 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([F:21])[C:18]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]2=[O:34])=[CH:17][C:3]=1[O:4][C:5]1[C:6]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1.[C:35](=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:1][C:2]1[CH:20]=[C:19]([F:21])[C:18]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]2=[O:34])=[CH:17][C:3]=1[O:4][C:5]1[C:6]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:35])=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 120567393-[2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-2-(methoxycarbonylmethoxy)pyridine2×

Product 1

HCID 12097345EpyrifenacilYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.60 g of 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(methoxycarbonyl)methoxypyridine [present compound 7-7], 0.13 g of sodium carbonate and 7.0 ml of ethanol was heated under reflux for 2 hours. It was cooled to room temperature, then, the solvent was distilled off under reduced pressure, and the resulted residue was subjected to silica gel chromatography to obtain 0.55 g of 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(ethoxycarbonyl)methoxypyridine [present compound 7-8].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-aebc68ee8b014af0b7f96e2f743ba717
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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