Toluene → 4-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-chloro-3-trifluoromethyl-5-methoxypyridine

HRID 243786Notes

Reaction equation

HRID 243786 reaction equation
P(Cl)(Cl)([Cl:3])=O.C1(C)C=CC=CC=1.[CH3:13][O:14][C:15]1[C:35]([O:36][CH3:37])=[C:34]([O:38][CH3:39])[CH:33]=[C:32]([CH3:40])[C:16]=1[C:17]([C:19]1[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][N+:22]([O-])=[CH:21][C:20]=1[O:30][CH3:31])=[O:18]>CN(C)C=O>[CH3:13][O:14][C:15]1[C:35]([O:36][CH3:37])=[C:34]([O:38][CH3:39])[CH:33]=[C:32]([CH3:40])[C:16]=1[C:17]([C:19]1[C:20]([O:30][CH3:31])=[CH:21][N:22]=[C:23]([Cl:3])[C:24]=1[C:25]([F:28])([F:27])[F:26])=[O:18]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 121513054-(2,3,4-trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine-N-oxide

Product 1

HCID 121514224-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-chloro-3-trifluoromethyl-5-methoxypyridineYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.8 ml (19 mmol) of phosphorus oxychloride was added at 0° C. to 4 ml of toluene and 8 ml of dimethylformamide, followed by stirring for 10 minutes, and then 4.0 g (10 mmol) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine-N-oxide was added, followed by stirring for 20 minutes. After stirring at room temperature for 2 hours, the reaction solution was charged into ice water to terminate the reaction. The aqueous layer was extracted with ethyl acetate, and then the organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 3.57 g (yield: 85%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-3-trifluoromethyl-5-methoxypyridine (melting point 117 to 119° C.).

Workup

  1. stirringby stirring for 20 minutes
  2. stirringAfter stirring at room temperature for 2 hours
  3. customto terminate
  4. customthe reaction
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. filtrationsubjected to filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dc96f880d0a6480e803687bd885cef25
Source dataset
uspto-grants-2014_02
Patent number
US08653277B2

Reaction notes

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