Water → Flumazenil

HRID 67350

Reaction equation

HRID 67350 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[CH:14]=[N:15][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:12]3[CH2:11][NH:10][C:9](=[O:22])[C:8]=2[CH:23]=1.[CH3:24]I.O>CN(C)C=O>[F:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[CH:14]=[N:15][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:12]3[CH2:11][N:10]([CH3:24])[C:9](=[O:22])[C:8]=2[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 6426758N-Desmethylflumazenil

Product 1

HCID 3373Flumazenil

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.1 g (2 mmol) of sodium hydride (55 percent oil dispersion) are suspended in 10 ml of dry dimethylformamide and treated with 0.5 g (1.7 mmol) of ethyl 8-fluoro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate. After completion of the gas evolution, 0.13 ml (2 mmol) of methyl iodide is added and the mixture is stirred at room temperature for 2 hours. The mixture is poured into ca 60 ml of water and extracted three times with 30 ml of chloroform each time. The combined chloroform extracts are washed with ca 30 ml of water, dried over magnesium sulphate and evaporated. After recrystallisation from ethyl acetate, there is obtained ethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 196°-197° C.

Workup

  1. extractionextracted three times with 30 ml of chloroform each time
  2. washThe combined chloroform extracts are washed with ca 30 ml of water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customAfter recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-974440ed808e4ce79112467fb0f8e4df
Source dataset
uspto-grants-1982_08
Patent number
US04346031

Linked notes

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