Hydrochloric Acid → HCID 23333591, compound

HRID 904202Notes

Reaction equation

HRID 904202 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7](=[O:16])[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=[O:11])[C:4]=2[CH:3]=1.[CH3:19][N:20](C)C=O.Cl>O>[C:19]([C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7](=[O:16])[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=[O:11])[C:4]=2[CH:3]=1)#[N:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 23333583HCID 23333583, compound

Product 1

HCID 23333591HCID 23333591, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5,6-dihydro-2-bromo-6,11-dioxodibenz[b,e]azepine (151 g), cuprous cyanide (49 g) and dimethylformamide (1.1 liters) was heated under refluxing for 8.5 hours. Then, the reaction mixture was cooled, and poured into a solution containing ferric chloride (200 g), conc. hydrochloric acid (50 ml) and water (500 ml) under stirring. The precipitated crystals were collected by filtration, washed with hydrochloric acid, and further washed thoroughly in water. Then, the crystals were dried at 60°-80° C. and dissolved in dimethylformamide (700 ml) with heating. The solution was filtered on heating, concentrated to 500 ml, and allowed to stand with the addition of dioxane (300 ml). The precipitated crystals were collected by filtration, washed with dioxane, then with n-hexane, and dried to obtain 5,6-dihydro-2-cyano-6,11-dioxodibenz[b,e]azepine (75 g).

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 8.5 hours
  3. temperatureThen, the reaction mixture was cooled
  4. additionpoured into a solution
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with hydrochloric acid
  7. washfurther washed thoroughly in water
  8. customThen, the crystals were dried at 60°-80° C.
  9. dissolutiondissolved in dimethylformamide (700 ml)
  10. temperaturewith heating
  11. filtrationThe solution was filtered
  12. temperatureon heating
  13. concentrationconcentrated to 500 ml
  14. additionto stand with the addition of dioxane (300 ml)
  15. filtrationThe precipitated crystals were collected by filtration
  16. washwashed with dioxane
  17. dry with materialwith n-hexane, and dried

Sources & evidence

ORD record
ord-107abd8dcb6d4467a83502053d9ff184
Source dataset
uspto-grants-1980_10
Patent number
US04230703

Reaction notes

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