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

HRID 223213Notes

Reaction equation

HRID 223213 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.[Cl:17]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl: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 31398ChlorosuccinimideHCID 199051164,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 205232833-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g (23.5 mmol) of 4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 30 ml of dimethylformamide are treated with 3.20 g (23.5 mmol) of N-chlorosuccinimide and stirred at room temperature for 1.5 hours and at 60° for 10 minutes. The clear brown solution is poured into about 200 ml of water and extracted three times with chloroform. The combined chloroform extracts are washed with water, dried over magnesium sulphate and evaporated. By chromatography of the residue on a silica gel column and subsequent recrystallization from ethyl acetate there is obtained 3-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 193°-194°.

Workup

  1. extractionextracted three times with chloroform
  2. washThe combined chloroform extracts are washed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customBy chromatography of the residue on a silica gel column and subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-8dc69c458f9f4209bf213feebaa9240b
Source dataset
uspto-grants-1982_10
Patent number
US04352818

Reaction notes

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