Methyl trifluoromethyl ketone → HCID 178465586, Verbindung

HRID 61948

Reaktionsgleichung

Reaktionsgleichung von HRID 61948
[F:1][C:2]([F:7])([F:6])[C:3]([CH3:5])=O.[Cl:8][C:9]1[C:10](=[N:15][NH2:16])[NH:11][CH:12]=[CH:13][CH:14]=1>>[F:1][C:2]([F:7])([F:6])[C:3](=[N:16][N:15]=[C:10]1[C:9]([Cl:8])=[CH:14][CH:13]=[CH:12][NH:11]1)[CH3:5]

Komponenten

4

Edukt 3

HCID 9871Methyl trifluoromethyl ketoneHCID 5561003-Chloro-2-hydrazinylpyridineHCID 178514363HCID 178514363, Verbindung

Produkt 1

HCID 178465586HCID 178465586, VerbindungAusbeute 66 %

Versuchsvorschrift

1,1,1-Trifluoroacetone (7.80 g, 69.6 mmol) was added to 3-chloro-2(1H)-pyridinone hydrazone (alternatively named (3-chloro-pyridin-2-yl)-hydrazine) (10 g, 69.7 mmol) at 20-25° C. After the addition was complete, the mixture was stirred for about 10 minutes. The solvent was removed under reduced pressure and the mixture partitioned between ethyl acetate (100 mL) and saturated aqueous sodium carbonate solution (100 mL). The organic layer was dried and evaporated. Chromatography on silica gel (eluted with ethyl acetate) gave the product as an off-white solid (11 g, 66% yield), m.p. 64-64.5° C. (after crystallization from ethyl acetate/hexanes).

Aufarbeitung

  1. additionAfter the addition
  2. customThe solvent was removed under reduced pressure
  3. customthe mixture partitioned between ethyl acetate (100 mL) and saturated aqueous sodium carbonate solution (100 mL)
  4. customThe organic layer was dried
  5. customevaporated
  6. customChromatography on silica gel (eluted with ethyl acetate) gave

Quellen und Nachweise

ORD-Eintrag
ord-fd96ed16c811405c94f4e00fbd70c812
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09445593B1

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