Acetic Anhydride → HCID 58786333, Verbindung

HRID 1375378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375378
[Li]CCCC.[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH2:15][N:16]([CH2:33][C:34]3[CH:42]=[CH:41][C:37]4[O:38][CH2:39][O:40][C:36]=4[CH:35]=3)[CH2:17][C:18]3[N:22]([CH2:23][CH2:24][CH2:25][CH3:26])[CH:21]=[N:20][C:19]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:14][C:9]=2[O:8][CH2:7]1.[CH3:43][C:44](OC(C)=O)=[O:45]>C1COCC1>[O:38]1[C:37]2[CH:41]=[CH:42][C:34]([CH2:33][N:16]([CH2:17][C:18]3[N:22]([CH2:23][CH2:24][CH2:25][CH3:26])[C:21]([C:44](=[O:45])[CH3:43])=[N:20][C:19]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:15][C:13]3[CH:12]=[CH:11][C:10]4[O:6][CH2:7][O:8][C:9]=4[CH:14]=3)=[CH:35][C:36]=2[O:40][CH2:39]1

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 673709331-(1,3-benzodioxol-5-yl)-N-(1,3-benzodioxol-5-ylmethyl)-N-[(1-butyl-4-phenyl-1H-imidazol-5-yl)methyl]methanamineHCID 178418339Butyllithium

Produkt 1

HCID 58786333HCID 58786333, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

n-BuLi (1.2 equivalents in 175 μl hexane) is added to a solution of 1-(1,3-benzodioxol-5-yl)-N-(1,3-benzodioxol-5-ylmethyl)-N-[(1-butyl-4-phenyl-1H-imidazol-5-yl)methyl]methanamine (118 mg), obtained as a minor product in Example 2, step 4, in 10 mL anhydrous THF under N2 at −78° C. The resulting mixture is stirred at −78° C. for 1 hour. Ac2O (118.4 mg, 1.2 equivalents) is added. The reaction mixture is stirred at −78° C. for 2 more hours, warmed to room temperature, and stirred overnight. The reaction is quenched with 5 mL of H2O and diluted with 20 mL ethyl acetate. The organic phase is collected, washed with brine, dried and concentrated. Purification via silica gel chromatography provides the title compound (Compound 8).

Aufarbeitung

  1. stirringThe reaction mixture is stirred at −78° C. for 2 more hours
  2. temperaturewarmed to room temperature
  3. stirringstirred overnight
  4. customThe reaction is quenched with 5 mL of H2O
  5. additiondiluted with 20 mL ethyl acetate
  6. customThe organic phase is collected
  7. washwashed with brine
  8. customdried
  9. concentrationconcentrated
  10. customPurification via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e784f02d51f743e9a440b012250d4b14
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169775B2

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