Triphenylphosphine → 6-Chloro-2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoic acid 4-pyridylthio ester

HRID 2396675

Reaction equation

HRID 2396675 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:11][C:12]2[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=2)[CH:5]=[CH:4][CH:3]=1.[CH:22]1[C:27]([S:28]C2C=CN=CC=2)=[CH:26][CH:25]=[N:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[N:24]1[CH:25]=[CH:26][C:27]([S:28][O:9][C:8](=[O:10])[C:7]2[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=2[O:11][C:12]2[N:13]=[C:14]([O:20][CH3:21])[CH:15]=[C:16]([O:18][CH3:19])[N:17]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 6046504,4'-Dipyridyl SulfideHCID 156119442-Chloro-6-((4,6-dimethoxypyrimidin-2-yl)oxy)benzoic acid

Product 1

HCID 543333746-Chloro-2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoic acid 4-pyridylthio esterYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

31.0 g of 6-chloro-2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoic acid, 22.0 g of 4,4'-dipyridylsulfide and 26.2 g of triphenylphosphine were suspended in 250 ml of toluene, and were violently stirred at room temperature for 2 hours. The reaction mixture was filtered, and the toluene was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography to obtain 36.0 g of the above identified compound as a white crystal (yield 90%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationthe toluene was distilled off under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified by silica gel column chromatography
  5. customto obtain 36.0 g of the

Sources & evidence

ORD record
ord-f24b90f1e2ae4c94b5aec90b4c1d5fe3
Source dataset
uspto-grants-1996_02
Patent number
US05494888

Linked notes

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