Sodium Bicarbonate → HCID 9842936, Verbindung

HRID 1166402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166402
CC1[N:3]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH:20]([C:22]([F:25])([F:24])[F:23])[N:19]=[C:18]3[C:26]3[C:27]([CH3:32])=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])C(C)=CC=1.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.O>[CH3:32][C:27]1[C:26]([C:18]2[N:17]([C:14]3[CH:15]=[CH:16][C:11]([S:8]([NH2:3])(=[O:10])=[O:9])=[CH:12][CH:13]=3)[CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[N:19]=2)=[CH:31][CH:30]=[CH:29][N:28]=1

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 22997798HCID 22997798, Verbindung

Produkt 1

HCID 9842936HCID 9842936, VerbindungAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A mixture of 3-[1-[4-[(2,5-dimethyl-1H-pyrrol-1-yl)sulfonyl]phenyl]-4,5-dihydro-4-(trifluoromethyl)-1H-imidazol-2-yl]-2-methylpyridine (Step 4) (4.6 g, 0.01 mol) in 75 mL of TFA and 25 mL of water was heated at reflux for 2 hours. The solution was cooled, treated with 400 mL of water and basified with sodium bicarbonate to pH 8. The aqueous phase was extracted with ethyl acetate (400 mL). The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5) to afford 4-[2-(2-methylpyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide as a white solid (3.0 g, 78%): mp (DSC): 235-237° C. Anal. Calc'd. for C16H13F3N3O2S: C, 50.26; H, 3.43; N, 14.65; S, 8.39. Found: C, 50.06; H,3.29; N, 14.4; S, 8.52.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe solution was cooled
  4. extractionThe aqueous phase was extracted with ethyl acetate (400 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe crude was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-baa3ebc49bfd4b6faf8ede6b7f40570a
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613789B2

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