Phosphorus oxychloride → 7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile

HRID 651571Notes

Reaction equation

HRID 651571 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([CH3:19])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH2:18])=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>O1CCOCC1>[Cl:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([CH3:19])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[N:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 14590422HCID 14590422, compound

Product 1

HCID 145904237-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

19.0 g 7-Chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide were suspended under stirring and argon atmosphere in 95 ml 1,4-dioxane and 6.58 ml phosphorous oxychloride were added in one portion. The reaction mixture was heated to reflux for one hour giving a yellow solution, which was concentrated at 50° C. under reduced pressure. The residue was digested in 100 ml deionized water for two hours at r.t. The precipitate (7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile) was filtered off, washed three times with 30 ml deionized water and dried under vacuum at 80° C. for 18 hours. Crude product: 17.3 g as a light yellow powder. m.p. 238.5-239.5° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for one hour
  3. customgiving a yellow solution, which
  4. concentrationwas concentrated at 50° C. under reduced pressure
  5. customfor two hours
  6. customat r.t
  7. filtrationThe precipitate (7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile) was filtered off
  8. washwashed three times with 30 ml
  9. customdried under vacuum at 80° C. for 18 hours

Sources & evidence

ORD record
ord-3d10f15bf6944cf694c96388f28ff015
Source dataset
uspto-grants-2001_08
Patent number
US06281353B1

Reaction notes

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