Water → 3-bromo-8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 223206Notes

Reaction equation

HRID 223206 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:11]=[CH:12][C:13]2[N:19]3[CH:20]=[N:21][CH:22]=[C:18]3[CH2:17][N:16]([CH3:23])[C:15](=[O:24])[C:14]=2[CH:25]=1.O>CN(C)C=O>[Br:1][C:22]1[N:21]=[CH:20][N:19]2[C:13]3[CH:12]=[CH:11][C:10]([F:9])=[CH:25][C:14]=3[C:15](=[O:24])[N:16]([CH3:23])[CH2:17][C:18]=12

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 229145898-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 205232943-bromo-8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.58 g of N-bromosuccinimide are added to 4.62 g (20 mmol) of 8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 100 ml of dimethylformamide and the mixture is stirred at room temperature for 2 hours. Subsequently, the mixture is poured into 500 ml of water and extracted several times with chloroform. The combined chloroform extracts are washed with water, dried over magnesium sulphate and evaporated. After recrystallization of the residue from ethyl acetate, there is obtained 3-bromo-8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 200°.

Workup

  1. extractionextracted several times with chloroform
  2. washThe combined chloroform extracts are washed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customAfter recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-91a6051bce924c19aa6dd30ef3464c20
Source dataset
uspto-grants-1982_10
Patent number
US04352818

Reaction notes

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