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

HRID 851647Notes

Reaction equation

HRID 851647 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 2 N 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 2 N 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-4cb2c24b147d4b489385de701f78e983
Source dataset
uspto-grants-1983_05
Patent number
US04386028

Reaction notes

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