Potassium Cyanide → HCID 54320306, compound

HRID 1154476Notes

Reaction equation

HRID 1154476 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+]>COC1C=CC=CC=1CO>[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:21]=[CH:10][CH:11]=[CH:15][C:16]=3[O:18][CH3:19])=[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 54320306HCID 54320306, compound

Reagents, catalysts & solvents 1

HCID 691542-Methoxybenzyl alcoholSolvent

Procedure

A mixture of 3.45 g (10 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 mg (1.5 mmol) of potassium cyanide and 20 ml of 2-methoxybenzyl alcohol is stirred at 110° for 36 hours, the resulting ethanol being removed in vacuo from time to time. The solvent is subsequently removed by distillation in a high vacuum and the residue is chromatographed on silica gel while eluting with ethyl acetate. By recrystallization from ethyl acetate/n-hexane there is obtained o-methoxybenzyl (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 178°-179°.

Workup

  1. customthe resulting ethanol being removed in vacuo from time to time
  2. customThe solvent is subsequently removed by distillation in a high vacuum
  3. customthe residue is chromatographed on silica gel
  4. washwhile eluting with ethyl acetate
  5. customBy recrystallization from ethyl acetate/n-hexane there

Sources & evidence

ORD record
ord-6c2a438661904f239dffb10ba24ef6c5
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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