hydroxylamine-O-sulfonic acid → 4-(2-Pyridin-3-yl-4-trifluoromethyl-imidazol-1-yl)-benzenesulfonamide

HRID 52370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52370
[CH3:1][Si:2]([CH3:30])([CH3:29])[CH2:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:16]=[C:15]2[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6].[N+:31](CCCC)(CCCC)(CCCC)CCCC.[F-].C([O-])(=O)C.[Na+].NOS(O)(=O)=O>C1COCC1.O.C(OCC)(=O)C>[CH3:1][Si:2]([CH3:30])([CH3:29])[CH2:3][CH2:4][S:5]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH:18]=[C:17]([C:19]([F:20])([F:21])[F:22])[N:16]=[C:15]2[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:12][CH:13]=1)(=[O:6])=[O:7].[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:15]2[N:14]([C:11]3[CH:12]=[CH:13][C:8]([S:5]([NH2:31])(=[O:7])=[O:6])=[CH:9][CH:10]=3)[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:16]=2)[CH:24]=1

Komponenten

9

Edukt 4

HCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 2724141Tetrabutylammonium FluorideHCID 105276743-[1-[4-[[2-(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine

Produkt 2

HCID 97993874-(2-Pyridin-3-yl-4-trifluoromethyl-imidazol-1-yl)-benzenesulfonamideAusbeute 173,5 %HCID 105276743-[1-[4-[[2-(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-[1-[4-[[2(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol -2-yl]pyridine was prepared from Example 30 with a method similar to that described in Example 48, Step 1. To a solution of 3-[1-[4-[[2-(trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (0.200 g, 0.46 mmol) in 1.0 mL of dry THF was added n-Bu4NF (1.38 mL of 1.0H THF solution, 1.38 mmol). The mixture was heated to reflux for 1 hour and cooled to room temperature. A solution of sodium acetate (0.17 g, 2.1 mmol) in 3 mL of water and hydroxylamine-O-sulfonic acid (0.26 g, 2.3 mmol) were added sequentially and the mixture was stirred for 1 hour. Water (7 mL) and ethyl acetate (7 mL) were added. The organic phase was separated and washed with saturated NaHCO3 solution, water, brine, dried over HgSO4 and filtered. The filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5) to give 0.147 g of 4-[2-(pyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide as a colorless solid (87%): mp(DSC) 213°-215 ° C. Anal. Calc'd. for C15H11F3N4O2S: C, 48.91; H, 3.01; N, 15.21; S, 8.71. Found: C, 48.58; H, 2.99; N, 14.87; S, 8.85.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customThe organic phase was separated
  4. washwashed with saturated NaHCO3 solution, water, brine
  5. dry with materialdried over HgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-d2a7222710944de9a90e8ba21d5528f2
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616601

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