Water → 3-bromo-7-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1606969Notes

Reaction equation

HRID 1606969 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:17])[N:9]([CH3:16])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][CH:15]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:18][C:15]1[N:14]=[CH:13][N:12]2[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=3[C:8](=[O:17])[N:9]([CH3:16])[CH2:10][C:11]=12

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 19851597HCID 19851597, compound

Product 1

HCID 198515903-bromo-7-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.38 g (50 mmol) of 7-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was stirred at room temperature for 40 minutes with 9.80 g (55 mmol) of N-bromosuccinimide in 80 ml of N,N-dimethylformamide. The reaction mixture was poured into 800 ml of water and the suspension obtained was filtered. The filter residue was rinsed with water and taken up in methylene chloride. The organic phase was dried over magnesium sulphate and evaporated. After chromatography of the residue on silica gel while eluting with ethyl acetate and recrystallization from ethyl acetate and hexane there was obtained 3-bromo-7-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 178°-179°.

Workup

  1. customthe suspension obtained
  2. filtrationwas filtered
  3. washThe filter residue was rinsed with water
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. customevaporated
  6. washAfter chromatography of the residue on silica gel while eluting with ethyl acetate and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-1d3beda2a8c944e6ae9d685e854530a7
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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