hydroxylamine-O-sulfonic acid → HCID 9842936, Verbindung

HRID 1353000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1353000
[CH3:1][C:2]1[C:7]([C:8]2[N:9]([C:17]3[CH:22]=[CH:21][C:20]([S:23](CC[Si](C)(C)C)(=[O:25])=[O:24])=[CH:19][CH:18]=3)[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:32](CCCC)(CCCC)(CCCC)CCCC.[F-].C([O-])(=O)C.[Na+].NOS(O)(=O)=O>C1COCC1.O.C(OCC)(=O)C>[CH3:1][C:2]1[C:7]([C:8]2[N:9]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([NH2:32])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

8

Edukt 4

HCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 2724141Tetrabutylammonium FluorideHCID 229977722-methyl-3-[1-[4-[[2-(trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine

Produkt 1

HCID 9842936HCID 9842936, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-methyl-3-[1-[4-[[2-(trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine from Step 1 (0.234 g, 0.5 mmol) in 1.5 mL of dry THF was added n-Bu4NF (1.5 mL of 1.0M THF solution, 1.5 mmol). The mixture was heated to reflux for 1 hour and cooled to room temperature. A solution of sodium acetate (0.19 g, 2.3 mmol) in 3 mL of water and hydroxylamine-o-sulfonic acid (0.28 g, 2.5 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 sat. NaHCO3 solution, water, and brine, dried over MgSO4 and filtered. The filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5) to give 0.16 g of 4-[2-(2-methylpyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide as a colorless solid (84%): mp 235–237° C. Anal. Calc'd. for C16H13F3N4O2S: C, 50.26; H, 3.43; N, 14.65; S, 8.39. Found: C, 50.06; H, 3.29; N, 14.44; S, 8.52.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customThe organic phase was separated
  4. washwashed with sat. NaHCO3 solution, water, and brine
  5. dry with materialdried over MgSO4
  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-5cd6c8e72d2148cab61629fa31f9c2e1
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220770B2

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