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

HRID 223214Notes

Reaction equation

HRID 223214 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][CH:16]=[C:4]2[CH2:3]1.[Br:17]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:17][C:16]1[N:15]=[CH:14][N:5]2[C:6]3[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=3[C:8](=[O:9])[N:2]([CH3:1])[CH2:3][C:4]=12

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 199051164,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198515313-bromo-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 g (93.8 mmol) of 4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6 -one in 100 ml of dimethylformamide are treated with 17.5 g (98 mmol) of N-bromosuccinimide and stirred at room temperature for 35 minutes. The solution is poured into water and extracted twice with chloroform. The chloroform extracts are washed several times with water, dried over magnesium sulphate and evaporated. After recrystallization from ethyl acetate, the residue yields 3-bromo-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 196°-198°.

Workup

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

Sources & evidence

ORD record
ord-e076ab1054344310900f1425cf0fc8c5
Source dataset
uspto-grants-1982_10
Patent number
US04352818

Reaction notes

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