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

HRID 44227Notes

Reaction equation

HRID 44227 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-eab0b563009d4394973e79b11856956b
Source dataset
uspto-grants-2013_09
Patent number
US08541407B2

Reaction notes

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