Potassium Cyanide → HCID 54376131, compound

HRID 1154474Notes

Reaction equation

HRID 1154474 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+].[Cl:28][C:29]1[CH:30]=C([CH:34]=[CH:35][CH:36]=1)CO>C(Cl)Cl>[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:34]=[CH:35][CH:36]=[C:29]([Cl:28])[CH:30]=3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 701173-Chlorobenzyl alcoholHCID 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 54376131HCID 54376131, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 of powdered potassium cyanide and 14.2 g of 3-chlorobenzyl alcohol is stirred at 130° for 48 hours, the mixture is diluted with about 20 ml of methylene chloride and chromatographed on about 300 g of silica gel while eluting with ethyl acetate. By crystallization from ethyl acetate and hexane there is obtained m-chlorobenzyl (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 114°-116°.

Workup

  1. customchromatographed on about 300 g of silica gel
  2. washwhile eluting with ethyl acetate
  3. customBy crystallization from ethyl acetate and hexane

Sources & evidence

ORD record
ord-e9ed4e6709994905931f55670745c17d
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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