6-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-one → 2,2-dimethyl-6-({4-[(4-propylphenyl)ethynyl]benzyl}amino)-4H-1,3-benzodioxin-4-one

HRID 551958Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551958
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[NH2:20][C:21]1[CH:22]=[CH:23][C:24]2[O:29][C:28]([CH3:31])([CH3:30])[O:27][C:26](=[O:32])[C:25]=2[CH:33]=1>>[CH3:30][C:28]1([CH3:31])[O:29][C:24]2[CH:23]=[CH:22][C:21]([NH:20][CH2:16][C:15]3[CH:18]=[CH:19][C:12]([C:11]#[C:10][C:7]4[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=4)=[CH:13][CH:14]=3)=[CH:33][C:25]=2[C:26](=[O:32])[O:27]1

Komponenten

3

Edukt 2

HCID 116153306-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-oneHCID 11736771HCID 11736771, Verbindung

Produkt 1

HCID 575545222,2-dimethyl-6-({4-[(4-propylphenyl)ethynyl]benzyl}amino)-4H-1,3-benzodioxin-4-oneAusbeute 25,2 %

Versuchsvorschrift

The title compound was prepared following procedure described in Example 1, step c) from 4-[(4-propylphenyl)ethynyl]benzaldehyde (1.53 g; 6.16 mmol) and 6-amino-2,2-dimethyl-benzo[1,3]dioxin-4-one (1.19 g; 6.16 mmol). Purification of the yellow solid (2.4 g) obtained by flash chromatography using silica gel (EtOAc:c-Hex 10:90 to 20:80) gave 660 mg (25%) of the title compound as a yellow solid. HPLC, Rt: 5.48 min (purity: 72.4%), 1H NMR (CDCl3) δ: 7.47 (d, J=7.5 Hz, 2H), 7.41 (d, J=8.1 Hz, 2H),: 7.31 (d, J=8.1 Hz, 2H), 7.08 (m, 3H), 6.70-6.79 (m, 2H), 4.25 (s, 2H), 2.57 (t, J=7.6 Hz, 2H), 1.62 (s, 6H), 1.55 (m, 2H), 0.86 (t, J=7.3 Hz, 3H).

Aufarbeitung

  1. customThe title compound was prepared following procedure
  2. customPurification of the yellow solid (2.4 g)
  3. customobtained by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9affbb71121741c58747c34487b2a5c8
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947851B2

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