2-(Phenylhydrazono)-propanedioyl dichloride → 2-[2,4-dioxo-5-phenyl-3-(phenyl-hydrazono)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide

HRID 1416117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416117
[CH:1]([N:4]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[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:30]1([NH:36][N:37]=[C:38]([C:42](Cl)=[O:43])[C:39](Cl)=[O:40])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[O:43]=[C:42]1[N:7]([CH2:6][C:5]([N:4]([CH:1]([CH3:3])[CH3:2])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[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:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:39](=[O:40])[C:38]1=[N:37][NH:36][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

4

Edukt 2

HCID 105144812-(Phenylhydrazono)-propanedioyl dichlorideHCID 10644060N-Isopropyl-N-(4-methoxy-phenyl)-2-(2-phenylamino-phenylamino)-acetamide

Produkt 1

HCID 544415272-[2,4-dioxo-5-phenyl-3-(phenyl-hydrazono)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamideAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Solutions of N-isopropyl-N-(4-methoxy-phenyl)-2-(2-phenylamino-phenylamino)-acetamide(3.00 g) in THF (30 mL) and 2-(phenyl-hydrazono) propandioyl dichloride (1.89 g) in THF (30 mL) were added concomitantly dropwise with stirring in an ice/methanol bath over a 30 minute period. After complete addition, the solution was allowed to warm to room temperature and stirred over night. The solvent was evaporated under reduced pressure and the resultant oil taken into ethyl acetate (250 mL), washed with saturated sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (4.28 g) as a yellow foam.

Aufarbeitung

  1. additionAfter complete addition
  2. stirringstirred over night
  3. customThe solvent was evaporated under reduced pressure
  4. washwashed with saturated sodium bicarbonate solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e4354b00f98d4d6e876d92e3ec470a0f
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05910495

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