Ammonia → HCID 20470725, compound

HRID 225108Notes

Reaction equation

HRID 225108 reaction equation
[C:1]([C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1)#[N:2].[C:18](Cl)(Cl)=[O:19].[NH3:22]>C1(C)C=CC=CC=1.C(O)C>[C:1]([C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:18]([NH2:22])=[O:19])[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6371PhosgeneHCID 23328936HCID 23328936, compound

Product 1

HCID 20470725HCID 20470725, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

With stirring, 21.8 g (0.1 mole) of 10-cyano-5H-dibenz[b,f]azepine are added to a solution of 19.8 g (0.2 mole) of phosgene in 700 ml of absolute toluene. The mixture is then stirred for 30 hours at 50°-53° C. and subsequently completely concentrated in a rotary evaporator, affording as residue crude 10-cyano-5H-dibenz[b,f]azepine-5-carbonyl chloride with a melting point of 148°-153° C. With stirring, the crude product is dissolved at 70° C. in 600 ml of absolute ethanol. Ammonia gas is then introduced into this solution in the course of 2 hours while constantly keeping the reaction mixture under reflux. The reaction mixture is then concentrated in a rotary evaporator and the residue is washed and dried. Recrystallisation from toluene yields 10-cyano-5H-dibenz[b,f]azepine-5-carboxamide with a melting point of 212°-215° C.

Workup

  1. stirringThe mixture is then stirred for 30 hours at 50°-53° C.
  2. concentrationsubsequently completely concentrated in a rotary evaporator
  3. customaffording as residue crude 10-cyano-5H-dibenz[b,f]azepine-5-carbonyl chloride with a melting point of 148°-153° C
  4. stirringWith stirring
  5. temperatureunder reflux
  6. concentrationThe reaction mixture is then concentrated in a rotary evaporator
  7. washthe residue is washed
  8. customdried
  9. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-9c59dc7e22534723a26de7547fe072dc
Source dataset
uspto-grants-1980_11
Patent number
US04235895

Reaction notes

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