Dimethyl-p-toluidine → 2-Chloro-4-(2,4-dimethoxy-benzyl)-7-bromo-3,4-dihydro-benzo[e][1,4]diazepin-5-one

HRID 351841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351841
[CH3:1][O:2][C:3]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:4]=1[CH2:5][N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([Br:18])[CH:16]=[CH:17][C:10]=2[NH:9][C:8](=O)[CH2:7]1.CN(C)C1C=CC(C)=CC=1.P(Cl)(Cl)([Cl:38])=O>C1(C)C=CC=CC=1>[Cl:38][C:8]1[CH2:7][N:6]([CH2:5][C:4]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:3]=2[O:2][CH3:1])[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([Br:18])[CH:16]=[CH:17][C:10]=2[N:9]=1

Komponenten

5

Edukt 3

HCID 7471Dimethyl-p-toluidineHCID 24813Phosphorus oxychlorideHCID 227134707-Bromo-4-(2,4-dimethoxybenzyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

Produkt 1

HCID 227134852-Chloro-4-(2,4-dimethoxy-benzyl)-7-bromo-3,4-dihydro-benzo[e][1,4]diazepin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-(2,4-Dimethoxy-benzyl)-7-bromo-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione (3.0 g, 7.4 mmol) and N,N-dimethyl-p-toluidine (2.1 mL, 14.8 mmol) were mixed in toluene (30 mL) and heated to 100° C. Then phosphorus oxychloride (745 μL, 8.1 mmol) was added dropwise and heating at 100° C. was continued for 2.5 h. The resulting dark red solution was evaporated and the residue dissolved in THF (10 mL) and used directly in the subsequent step.

Aufarbeitung

  1. temperatureheating at 100° C.
  2. customThe resulting dark red solution was evaporated
  3. dissolutionthe residue dissolved in THF (10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-6b8915960bd74c35be7caac5e7f40218
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743789B2

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