Chloroacetic anhydride → 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1377975Notes

Reaction equation

HRID 1377975 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][C:16]([C:17](=[N:19][OH:20])[NH2:18])=[C:4]2[CH2:3]1.[Cl:21][CH2:22][C:23](OC(=O)CCl)=O>CN(C)C=O>[Cl:21][CH2:22][C:23]1[O:20][N:19]=[C:17]([C:16]2[N:15]=[CH:14][N:5]3[C:6]4[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=4[C:8](=[O:9])[N:2]([CH3:1])[CH2:3][C:4]=23)[N:18]=1

Participants

4

Reactant 2

HCID 10946Chloroacetic anhydrideHCID 566103035,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime

Product 1

HCID 229143143-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-oneYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.60 g (16.95 mmol) 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime were stirred with 3.19 g (18.65 mmol) of chloroacetic anhydride in 25 ml of N,N-dimethylformamide at room temperature for 30 minutes and at 105° for 2 hours. The reaction mixture was evaporated, the residue was dissolved in methylene chloride and the solution was washed with saturated sodium bicarbonate solution. After drying over magnesium sulfate the solution was concentrated and the crystalline residue was chromatographed on silica gel while eluting with ethyl acetate. There were obtained 3.94 g (70%) of 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 208°-209°.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washthe solution was washed with saturated sodium bicarbonate solution
  4. dry with materialAfter drying over magnesium sulfate the solution
  5. concentrationwas concentrated
  6. customthe crystalline residue was chromatographed on silica gel
  7. washwhile eluting with ethyl acetate

Sources & evidence

ORD record
ord-e0f996ebb5b84ff2b487753dc519e41f
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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