HCID 21764315, compound → ethyl 5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

HRID 67604Notes

Reaction equation

HRID 67604 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[N:9]2[CH:18]=[N:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:8]2[CH2:7]1>FC(F)(F)C(O)=O>[O:13]=[C:12]1[C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[N:9]2[CH:18]=[N:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:8]2[CH2:7][NH:6]1

Participants

3

Reactant 1

HCID 21764315HCID 21764315, compound

Product 1

HCID 21764316ethyl 5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

90 g (214 mmol) of ethyl 5,6-dihydro-5-(2,4-dimethoxybenzyl)-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate are heated to reflux while stirring for 3 hours in 300 ml of trifluoroacetic acid. After evaporation in vacuo, the residue is treated with water and made alkaline with 10 percent potassium carbonate solution. The separated material is filtered off under suction, washed with water and dried in vacuo. After recrystallisation from chloroform/hexane, there is obtained ethyl 5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 248°-250° C.

Workup

  1. temperatureto reflux
  2. customAfter evaporation in vacuo
  3. additionthe residue is treated with water
  4. filtrationThe separated material is filtered off under suction
  5. washwashed with water
  6. customdried in vacuo
  7. customAfter recrystallisation from chloroform/hexane

Sources & evidence

ORD record
ord-5db099e749724fe78a68bf76d819b421
Source dataset
uspto-grants-1982_08
Patent number
US04346036

Reaction notes

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