Water → HCID 178450115, Verbindung

HRID 1604699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604699
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:33]=[CH:32][CH:31]=[CH:30][C:22]=4[O:23][CH:24]([CH2:27][CH2:28][CH3:29])[C:25]#[N:26])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[N-:34]=[N+:35]=[N-:36].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:33]=[CH:32][CH:31]=[CH:30][C:22]=4[O:23][CH:24]([C:25]4[NH:36][N:35]=[N:34][N:26]=4)[CH2:27][CH2:28][CH3:29])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 196037652-{2-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanenitrile

Produkt 1

HCID 178450115HCID 178450115, VerbindungAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

2-{2-{[2-(4-tert-Butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanenitrile (430 mg) was dissolved in dimethylformamide (5 ml), and sodium azide (364 mg) and ammonium chloride (0.3 g) were added. The mixture was stirred at 120° C. for three hours. The reaction mixture was cooled and poured into water and extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate again and the combined organic layer was washed with brine and dried over magnesium sulfate. After concentration, the crude product was purified on a silica gel column (15 g) eluting with a mixed solvent of methylene chloride and methanol (2% vol.) to give 2-(4-tert-butylthiazol-2-yl)-5-{2-[1-(1H-tetrazol-5-yl)butoxy]phenylmethoxy}benzofuran (400 mg).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate again
  4. washthe combined organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationAfter concentration
  7. customthe crude product was purified on a silica gel column (15 g)
  8. washeluting with a mixed solvent of methylene chloride and methanol (2% vol.)

Quellen und Nachweise

ORD-Eintrag
ord-771fd0a15eb342df9572643e26410ad2
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994378

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