Propanedioyl dichloride → 2-(2,4-Dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl acetamide

HRID 343090

Reaktionsgleichung

Reaktionsgleichung von HRID 343090
[CH:1]([N:4]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:5](=[O:21])[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:3])[CH3:2].[C:28](Cl)(=[O:33])[CH2:29][C:30](Cl)=[O:31]>C1COCC1>[O:31]=[C:30]1[N:7]([CH2:6][C:5]([N:4]([CH:1]([CH3:3])[CH3:2])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:28](=[O:33])[CH2:29]1

Komponenten

4

Edukt 2

HCID 74269Propanedioyl dichlorideHCID 10784706N-Isopropyl-N-phenyl-2-(2-phenylamino-phenylamino)-acetamide

Produkt 1

HCID 108124012-(2,4-Dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl acetamideAusbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To 20 mL of THF at 0° C. is added dropwise over 10 min simultaneously a solution of 1.97 g (5.48 mmol) of N-isopropyl-N-phenyl-2-(2-phenylamino-phenylamino) acetamide in 20 mL of THF and 0.53 mL (5.48 mmol) of malonyl dichloride in 20 mL of THF. The resulting red-brown solution is stirred at RT for 5.5 h and the solvent removed in vacuo. Purification of the resulting brown oil by silica gel flash chromatography (50 to 75% ethyl acetate/petroleum ether) followed by recrystallization from ethyl acetate/petroleum ether gave 0.84 g of the title compound as a white powder: mp. 199°-200° C.; 1H NMR (CDCl3, 300 MHz) δ7.6-7.2 (m, 12H), 7.09 (t, 1H, J=8), 6.90 (d, 1H, J=8), 5.05 (m, 1H), 4.38 (d, 1H, J=17), 4.04 (d, 1H, J=17), 3.54 (dd, 2H, J=5, 22), 1.10 (d, 6H, J=7); low resolution MS (FAB) m/e 428 (MH+).

Aufarbeitung

  1. customthe solvent removed in vacuo
  2. customPurification of the resulting brown oil by silica gel flash chromatography (50 to 75% ethyl acetate/petroleum ether)
  3. customfollowed by recrystallization from ethyl acetate/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-9e43e6a3e5754d339fca2990fe41d7ef
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859007

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