Sodium Hydroxide → HCID 21875586, Verbindung

HRID 50435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50435
CO[C:3]1[CH:35]=[CH:34][C:6]2[NH:7][CH:8]([CH2:32][CH3:33])[N:9]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:19]([NH:21][S:22]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=4)(=[O:24])=[O:23])=[O:20])=[CH:12][CH:11]=3)[C:5]=2[CH:4]=1.[OH-:36].[Na+]>Br>[CH2:32]([C:8]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:19]([NH:21][S:22]([C:25]3[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=3)(=[O:24])=[O:23])=[O:20])=[CH:12][CH:11]=2)[C:5]2[CH:4]=[CH:3][C:35]([OH:36])=[CH:34][C:6]=2[N:7]=1)[CH3:33]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 218757625-Methoxy-2-ethyl-3-(4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)amino]ethyl}phenyl)-1H-benzimidazole

Produkt 1

HCID 21875586HCID 21875586, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 260Hydrogen BromideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 1-[4-(2-chloroethyl)phenyl]-2-ethyl-5-methoxy-1H-benzimidazole (step 5 of Example 71, 600 mg, 1.9 mmol) in 48% hydrobromic acid (60 mL) was stirred at 100° C. for 6 h. After cooling, the mixture was neutralized with 2N aqueous NaOH and extracted with ethyl acetate (100 mL). The organic layer was washed with brine (50 mL), dried (Na2SO4), and concentrated to afford 890 mg (quant.) of the title compound as pale yellow solids: 1H-NMR (CDCl3) δ 7.64 (4H, s), 7.16 (2H, m), 6.97-7.01 (1H, m), 3.86 (2H, t, J=7.1 Hz), 3.30 (2H, t, J=7.1 Hz), 2.92 (2H, q, J=7.8 Hz), 1.29 (3H, t, J=7.8 Hz).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-91e3bad74386410bb9e6836fb30362c0
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710054B2

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