Potassium Cyanide → HCID 54254734, compound

HRID 1154458Notes

Reaction equation

HRID 1154458 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C-:25]#N.[K+]>C(O)C#C>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH2:19][C:20]#[CH:25])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 53890667ethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepine-1-carboxylate

Product 1

HCID 54254734HCID 54254734, compound

Reagents, catalysts & solvents 1

HCID 7859Propargyl alcoholSolvent

Procedure

A mixture of 6.92 g (0.02 mol) of ethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 100 ml of propargyl alcohol and 0.4 g of potassium cyanide is heated to boiling under reflux for 4 hours, 75 ml of the solvent are then removed by distillation, 75 ml of propargyl alcohol are added to the mixture and the resulting mixture is heated to boiling under reflux for a further 16 hours. The mixture is concentrated, 25 ml of water are added to the residue and the mixture obtained is extracted three times with 25 ml of chloroform each time, the chloroform solution is dried over magnesium sulphate and evaporated. The residue is chromatographed on silica gel while eluting with ethyl acetate. By recrystallization from ethyl acetate there is obtained 2-propynyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 213°-214°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. custom75 ml of the solvent are then removed by distillation, 75 ml of propargyl alcohol
  4. additionare added to the mixture
  5. temperaturethe resulting mixture is heated
  6. temperatureunder reflux for a further 16 hours
  7. concentrationThe mixture is concentrated
  8. addition25 ml of water are added to the residue
  9. customthe mixture obtained
  10. extractionis extracted three times with 25 ml of chloroform each time
  11. dry with materialthe chloroform solution is dried over magnesium sulphate
  12. customevaporated
  13. customThe residue is chromatographed on silica gel
  14. washwhile eluting with ethyl acetate
  15. customBy recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-dc18b08f62a64bee8132c77b14f0d493
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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