Potassium Cyanide → benzyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

HRID 1154455Notes

Reaction equation

HRID 1154455 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-]#N.[K+]>C(O)C1C=CC=CC=1>[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]3[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=3)=[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 54076798benzyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Procedure

5 g (14.5 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, 70 mg of powdered potassium cyanide and 20 ml of benzyl alcohol are stirred at 110° for 1 hour, evaporated to dryness and the residue is taken up in chloroform. The solution is washed with water, dried over magnesium sulphate and evaporated. By recrystallization from ethanol and ether there is obtained benzyl (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 141°-142°.

Workup

  1. customevaporated to dryness
  2. washThe solution is washed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customBy recrystallization from ethanol and ether

Sources & evidence

ORD record
ord-37346b1705224259ae919e92bc89035e
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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