Sodium Methoxide → HCID 15766881, compound

HRID 1957243Notes

Reaction equation

HRID 1957243 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([N:19](S(C)(=O)=O)[S:20]([CH3:23])(=[O:22])=[O:21])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C[O-].[Na+]>CO>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 19068742HCID 19068742, compound

Product 1

HCID 15766881HCID 15766881, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.6 g (7.78 mmol) of 3-chloro-2-[4-chloro-3-bis-(methylsulfonyl)aminophenyl]-5-trifluoromethylpyridine (prepared as in Example 13) and 100 mg of sodium methoxide in 100 ml of methanol were stirred at 20°-25° C. for three hours. Then most of the methanol was distilled off under reduced pressure. The residue was taken up in dilute hydrochloric acid, after which the product was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The oily residue was treated with ether/petroleum ether to afford 1.6 g (53%) of colorless crystals of melting point 133°-134° C.

Workup

  1. distillationThen most of the methanol was distilled off under reduced pressure
  2. extractionafter which the product was extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated
  5. additionThe oily residue was treated with ether/petroleum ether

Sources & evidence

ORD record
ord-c696d3f6579e4693ae2d8debd2aac310
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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