Potassium Cyanide → HCID 54063757, compound

HRID 1154491Notes

Reaction equation

HRID 1154491 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][CH:20]=[CH2:25])=[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 54063757HCID 54063757, compound

Reagents, catalysts & solvents 1

HCID 7858Allyl AlcoholSolvent

Procedure

A mixture of 6.9 g (0.02 mmol) 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 allyl alcohol and 0.5 g of potassium cyanide is heated to boiling ii under reflux for 4 hours, then concentrated to half of the volume, 50 ml of allyl alcohol are added and the resulting mixture is heated to boiling under reflux for a further 10 hours. The mixture is evaporated, the residue is dissolved in chloroform, the chloroform solution is washed with water, the chloroform phase is dried over magnesium sulphate and evaporated. The residue is chromatographed on silica gel while eluting with ethyl acetate and then crystallized from ethyl acetate/hexane. There is obtained allyl (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 122-123°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. concentrationconcentrated to half of the volume, 50 ml of allyl alcohol
  4. additionare added
  5. temperaturethe resulting mixture is heated
  6. temperatureunder reflux for a further 10 hours
  7. customThe mixture is evaporated
  8. dissolutionthe residue is dissolved in chloroform
  9. washthe chloroform solution is washed with water
  10. dry with materialthe chloroform phase is dried over magnesium sulphate
  11. customevaporated
  12. customThe residue is chromatographed on silica gel
  13. washwhile eluting with ethyl acetate
  14. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e291d21e008248b4a22ade2e0af431e7
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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