Dimethylformamide → Fluoromidine

HRID 437396

Reaktionsgleichung

Reaktionsgleichung von HRID 437396
CN(C)C=O.O[N:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]1[C:16]([F:19])([F:18])[F:17].S(Cl)([Cl:22])=O>>[Cl:22][C:13]1[CH:14]=[C:15]2[NH:7][C:8]([C:16]([F:19])([F:18])[F:17])=[N:9][C:10]2=[N:11][CH:12]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 214284001-hydroxy-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine

Produkt 1

HCID 911208Fluoromidine

Versuchsvorschrift

Dimethylformamide (2 milliliters) was added to 4 grams of 1-hydroxy-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine in 10 milliliters of thionyl chloride. The resulting reaction mixture was heated on a steam bath overnight. Solvent was removed and the residue shaken with 50 milliliters of water and filtered. The residue was then taken up in sodium hydroxide solution, filtered and acidified to pH 3, shaken with three 150-milliliter portions of diethyl ether, and dried over magnesium sulfate. Solvent was evaporated, yielding the desired 6-chloro-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine, m.p., 290°-2° C., with sublimation from 260° C.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas heated on a steam bath overnight
  3. customSolvent was removed
  4. filtrationfiltered
  5. filtrationfiltered
  6. stirringshaken with three 150-milliliter portions of diethyl ether
  7. dry with materialdried over magnesium sulfate
  8. customSolvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-29557544ddf240a6b576e15879ef0737
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04031107

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