4-Fluorobenzoic Acid → HCID 22339496, compound

HRID 1006214Notes

Reaction equation

HRID 1006214 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:18]2[C:23](=[O:24])[NH:22][C:21](=[O:25])[CH:20]=[N:19]2)[CH:5]=[C:6]([CH3:17])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=1>O>[Cl:1][C:2]1[CH:3]=[C:4]([N:18]2[C:23](=[O:24])[NH:22][C:21](=[O:25])[CH:20]=[N:19]2)[CH:5]=[C:6]([CH3:17])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:27]([F:26])=[CH:28][CH:29]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 99734-Fluorobenzoic AcidHCID 22339732HCID 22339732, compound

Product 1

HCID 22339496HCID 22339496, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-{3-chloro-4-[4-methoxy-phenoxy]-5-methyl-phenyl}-2H-[1,2,4]triazine-3,5-dione (1.2 g) and p-fluorobenzoic acid (0.8 g) in Eaton's acid (5 mL) was heated at 60° C. for 4 h. The resulting red solution was cooled to 0° C., water (30 mL) added and the suspension stirred at room temperature for 30 min. The mixture was extracted with ethyl acetate (2×), the combined organic layers washed with saturated aqueous sodium bicarbonate, dried (Na2SO4), concentrated in vacuo and flashed chromatographed on silica gel (25-40% THF/hexanes) to afford the title compound of Step A as a off-white foam, 1.1 g. MS Calc.:481.9; Found:481.8.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×)
  2. washthe combined organic layers washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customflashed chromatographed on silica gel (25-40% THF/hexanes)

Sources & evidence

ORD record
ord-ad6cf019a5134b62b6b5d7755cf7ab68
Source dataset
uspto-grants-2004_09
Patent number
US06787652B1

Reaction notes

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