7-Bromo-4-methyl-3,4-dihydro-1H-benzo[E][1,4]diazepine-2,5-dione → HCID 20487135, compound

HRID 1995514Notes

Reaction equation

HRID 1995514 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:15]=1.[Cu][C:17]#[N:18]>N1C=CC=CC=1>[C:17]([C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:15]=1)#[N:18]

Participants

4

Reactant 2

HCID 52976447-Bromo-4-methyl-3,4-dihydro-1H-benzo[E][1,4]diazepine-2,5-dioneHCID 178418546HCID 178418546, compound

Product 1

HCID 20487135HCID 20487135, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

15.0 g of 7-bromo-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione and 7.5 g of copper (I) cyanide (freshly prepared) are mixed well in a mortar and heated from 165° to 195° with 7.2 ml of dry pyridine (freshly distilled over potassium hydroxide) under argon over a period of 3 hours. After cooling to 150°, the solid mass is dissolved in about 250 ml of boiling dimethylformamide. The mixture is left to cool, poured into 800 ml of ice-water and extracted three times with 500 ml of chloroform each time. The organic extracts are washed with 250 ml of 2N hydrochloric acid and three times with 500 ml of water each time, dried in the presence of active carbon and evaporated. The residue is dissolved in about 1 l of methanol. The solution is concentrated to a volume of 250 ml, treated with active carbon and cooled to 5°. The precipitated material is filtered off under suction and dried, there being obtained 7-cyano-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione as white crystals of melting point 256°-258°.

Workup

  1. additionare mixed well in a mortar
  2. distillationfreshly distilled over potassium hydroxide) under argon over a period of 3 hours
  3. temperatureAfter cooling to 150°
  4. dissolutionthe solid mass is dissolved in about 250 ml of boiling dimethylformamide
  5. waitThe mixture is left
  6. temperatureto cool
  7. additionpoured into 800 ml of ice-water
  8. extractionextracted three times with 500 ml of chloroform each time
  9. washThe organic extracts are washed with 250 ml of 2N hydrochloric acid and three times with 500 ml of water each time
  10. customdried in the presence of active carbon
  11. customevaporated
  12. dissolutionThe residue is dissolved in about 1 l of methanol
  13. concentrationThe solution is concentrated to a volume of 250 ml
  14. additiontreated with active carbon
  15. temperaturecooled to 5°
  16. filtrationThe precipitated material is filtered off under suction
  17. customdried

Sources & evidence

ORD record
ord-69de94cae7ba4e348f415eb721081cef
Source dataset
uspto-grants-1983_09
Patent number
US04405516

Reaction notes

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