Hydrochloric Acid → HCID 178478067, Verbindung

HRID 2232962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2232962
[Al](C)(C)C.[Cl:5][C:6]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:7]=1[C:8]#[N:9].[N:15]([Si](C)(C)C)=[N+:16]=[N-:17].Cl>C1(C)C=CC=CC=1>[Cl:5][C:6]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:7]=1[C:8]1[NH:17][N:16]=[N:15][N:9]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 78378AzidotrimethylsilaneHCID 7365672,3-DichlorobenzonitrileHCID 16682925Trimethylaluminum

Produkt 1

HCID 178478067HCID 178478067, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 2.0 M solution of Al(CH3)3 in toluene (35 mL) was treated with 2,3-dichlorobenzonitrile (8.00 g, 37.2 mmol), azidotrimethylsilane (5.14 g, 44.6 mmol) slowly, and heated at 80° C. for 16 hours behind a blast shield. The mixture was cooled to 0° C. and treated with 2N HCl (100 mL) dropwise over 1 hour. The mixture was allowed to warm to ambient temperature and extracted twice with ethyl acetate (100 mL). The combined organic phases were dried over Na2SO4, filtered through a ½″ pad of silica gel, and the filtrate was evaporated under reduced pressure. The residue was purified by recrystallization from ethyl acetate/hexanes to provide the title compound. MS (DCI/NH3) m/z 215 (M)+; 1H NMR (DMSO-d6) δ 7.59 (t, 1H, J=8.0 Hz), 7.79 (dd, 1H, J=7.8, 1.7 Hz), 7.92 (dd, 1H, J=8.1, 1.7 Hz).

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. temperatureto warm to ambient temperature
  3. extractionextracted twice with ethyl acetate (100 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered through a ½″ pad of silica gel
  6. customthe filtrate was evaporated under reduced pressure
  7. customThe residue was purified by recrystallization from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d226031809ac4f78953f3dc8ab307577
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709469B2

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