Ethanol → 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime

HRID 2164778Notes

Reaction equation

HRID 2164778 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][N:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[N:9]([CH3:18])[CH2:8][C:7]=12)#[N:2].Cl.[NH2:20][OH:21].C(O)C.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:18][N:9]1[C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:6]2[CH:5]=[N:4][C:3]([C:1](=[N:20][OH:21])[NH2:2])=[C:7]2[CH2:8]1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 139845425-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.0125 mole 3-cyano-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine, 1.1 g of hydroxylamine hydrochloride, 200 ml of 99% ethanol and 5.2 ml of a 20% potassium carbonate solution in water was refluxed for 22 hours. The reaction mixture was filtered and the filtrate was concentrated. The residue was treated with 100 ml of water and the crystalline solid was filtered off and was washed with water.

Workup

  1. temperaturewas refluxed for 22 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. additionThe residue was treated with 100 ml of water
  5. filtrationthe crystalline solid was filtered off
  6. washwas washed with water

Sources & evidence

ORD record
ord-3dec5ff6eeb34bef814064c85b4130e1
Source dataset
uspto-grants-1985_03
Patent number
US04507313

Reaction notes

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