Pyridine → 6,6-Difluoro-5-methyl-5-hexenyl 6-(toluene-4-sulfonylamino)nicotinate

HRID 917370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917370
N1C=CC=CC=1.[NH2:7][C:8]1[CH:25]=[CH:24][C:11]([C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:23])=[C:20]([F:22])[F:21])=[O:13])=[CH:10][N:9]=1.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>Cl>[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32]([NH:7][C:8]2[CH:25]=[CH:24][C:11]([C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:23])=[C:20]([F:22])[F:21])=[O:13])=[CH:10][N:9]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 230203546,6-Difluoro-5-methyl-5-hexenyl 6-aminonicotinate

Produkt 1

HCID 230202826,6-Difluoro-5-methyl-5-hexenyl 6-(toluene-4-sulfonylamino)nicotinateAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

To 5 ml of pyridine was dissolved 0.62 g (2.3 mmol) of 6,6-difluoro-5-methyl-5-hexenyl 6-aminonicotinate, followed by the addition of 0.48 g (2.5 mmol) of toluene-4-sulfonylchloride under ice-cooling, stirring for 10 minutes and then stirring at room temperature for 15 hours. The reaction liquid was then poured in 5% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 0.88 g (yield: 90%) of 6,6-difluoro-5-methyl-5-hexenyl 6-(toluene-4-sulfonylamino)nicotinate.

Aufarbeitung

  1. temperaturecooling
  2. stirringstirring at room temperature for 15 hours
  3. customThe reaction liquid
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  7. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-d9945211f11440aca5ad09f2c632ea28
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273878B2

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