Potassium Cyanide → methyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

HRID 67320Notes

Reaction equation

HRID 67320 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]([O:19][CH2:20]C)=[O:18])=[C:4]2[CH2:3]1.[C-]#N.[K+]>CO>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:4]2[CH2:3]1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 127597Ro 14-7437

Product 1

HCID 10378479methyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

285 mg (1 mmol) of ethyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate and 66 mg of potassium cyanide are heated to boiling under reflux for 24 hours in 10 ml of methanol. Then, the mixture is concentrated on a rotary evaporator, the residue is partitioned between water and chloroform, extracted twice with chloroform, the chloroform phase is dried over magnesium sulphate and evaporated. There is obtained methyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 212°-214° C. This product is uniform according to thin-layer chromatography.

Workup

  1. concentrationThen, the mixture is concentrated on a rotary evaporator
  2. customthe residue is partitioned between water and chloroform
  3. extractionextracted twice with chloroform
  4. dry with materialthe chloroform phase is dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-2343817238154b91a71b7b1a643bedcf
Source dataset
uspto-grants-1982_08
Patent number
US04346030

Reaction notes

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