Water → 7-Chloro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a]-[4,1]benzoxazepine-3-amidoxime

HRID 1110934Notes

Reaction equation

HRID 1110934 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:18])[O:9][CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[N:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:26][OH:27].O>C(O)(C)C>[Cl:1][C:2]1[C:7]2[C:8](=[O:18])[O:9][CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](=[N:26][OH:27])[NH2:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 537107387-chloro-5,6-dihydro-6-oxo-4H-imidazo [1,5-a][4,1]benzoxazepine-3-carbonitrile

Product 1

HCID 537468867-Chloro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a]-[4,1]benzoxazepine-3-amidoximeYield 68.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 7-chloro-5,6-dihydro-6-oxo-4H-imidazo [1,5-a][4,1]benzoxazepine-3-carbonitrile (16.86 g, 0.06 mole), potassium carbonate (13.5 g, 0.9 mole) and hydroxylamine hydrochloride (4.6 g, 0.06 mole) in isopropanol (843 ml) containing water (13.5 ml) was stirred at room temperature for 4 days. The reaction mixture was then concentrated to a volume of 256 ml by distillation, cooled to room temperature and water (256 ml) added. The resulting mixture was cooled at 0° C. for 1 hour and the solid collected, washed with water and dried in vacuo at 50° C. to give the product (12 g, 63%), m.p. 252°-254° C.

Workup

  1. concentrationThe reaction mixture was then concentrated to a volume of 256 ml by distillation
  2. temperaturecooled to room temperature
  3. additionwater (256 ml) added
  4. temperatureThe resulting mixture was cooled at 0° C. for 1 hour
  5. customthe solid collected
  6. washwashed with water
  7. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-0960f4795d674c8481423e785a503b3a
Source dataset
uspto-grants-1990_12
Patent number
US04977258

Reaction notes

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