Phosphorus pentachloride → 6-chloro-11H-benzo[e]pyrido[3,2-b][1,4]diazepine

HRID 44227

Reaktionsgleichung

Reaktionsgleichung von HRID 44227
[N:1]1[C:11]2[NH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=O)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:18]>ClCCl>[Cl:18][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[NH:10][C:11]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[N:6]=1

Komponenten

4

Edukt 2

HCID 24819Phosphorus pentachlorideHCID 701695,11-Dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one

Produkt 1

HCID 1361637716-chloro-11H-benzo[e]pyrido[3,2-b][1,4]diazepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one (18 g, 85.3 mmol) and PCl5 (20.5 g) in dichloromethane (650 mL) was stirred at reflux until the starting material was all consumed (use LC/MS to follow the reaction). The reaction mixture was concentrated in vacuo to half volume and the resulting solid was collected by filtration and washed with dichloromethane. The filtrate was further concentrated and a second crop was similarly obtained and combined. The 6-chloro-11H-benzo[e]pyrido[3,2-b][1,4]diazepine was obtained as a yellow solid (total 14 g, 71%). LCMS [M+H]: 230.

Aufarbeitung

  1. temperatureat reflux until the starting material
  2. customall consumed (use LC/MS
  3. customthe reaction)
  4. concentrationThe reaction mixture was concentrated in vacuo to half volume
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with dichloromethane
  7. concentrationThe filtrate was further concentrated
  8. customa second crop was similarly obtained

Quellen und Nachweise

ORD-Eintrag
ord-eab0b563009d4394973e79b11856956b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541407B2

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