Benzoyl chloride → HCID 21071399, Verbindung

HRID 1371920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371920
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C1C=CN=CC=1.ClCCl>[C:24]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]1[C:14](=[O:23])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]1=[O:22])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

5

Edukt 2

HCID 7412Benzoyl chlorideHCID 21071398HCID 21071398, Verbindung

Produkt 1

HCID 21071399HCID 21071399, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Combine 2-(2-(5-amino-1H-indol-3-yl)ethyl)isoindole-1,3-dione (0.5 g, 1.64 mmol) and 4-dimethylaminopyridine (0.3 g, 2.5 mmol) and dissolve in 30 mL dichloromethane and cool to 0° C. Treat the reaction mixture with benzoyl chloride (276 mg, 1.96 mmol) and stir overnight during which the temperature was allowed to warm to room temperature. Concentrate to residue and chromatograph the residue on silica gel eluting with 0.5% MeOH in CHCl3 to give the title compound as a solid: ISMS 410 (M+1); 1H NMR (CDCl3) 7.86–7.85 (m, 2H), 7.79 (s, 1H), 7.72–7.68 (m, 2H), 7.60–7.57 (m, 2H), 7.46–7.42 (m, 1H), 7.4–7.36 (m, 3H), 7.13–7.11 (d, 1H), 6.89–6.88 (m, 1H), 3.88–3.84 (t, 2H), 3.00–2.97 (t, 2H).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. concentrationConcentrate to residue

Quellen und Nachweise

ORD-Eintrag
ord-c36542520af9421593af7df1ffa8ef2e
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157488B2

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