Sodium Carbonate → (S)-8-bromo-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime

HRID 1378166Notes

Reaction equation

HRID 1378166 reaction equation
[Br:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]3[CH2:19][CH2:18][C@H:10]3[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-].[Na+].[Na+].Cl.[NH2:28][OH:29]>C(O)C.O>[Br:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]3[CH2:19][CH2:18][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](=[N:28][OH:29])[NH2:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 54289267(S)-8-bromo-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile

Product 1

HCID 53634407(S)-8-bromo-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoximeYield 51.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

13 g (39.5 mmol) of (S)-8-bromo-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile were stirred with 7.5 g (71 mmol) of sodium carbonate and 5.7 g (82 mmol) of hydroxylamine hydrochloride in 200 ml of ethanol and 40 ml of water at 50° for 1 hour and at 75° for 10 minutes. After dilution with 50 ml of water the suspension was suction filtered, whereupon the crystals were dried. There were obtained 7.33 g (51%) of (S)-8-bromo-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime of m.p. 265°-266°.

Workup

  1. filtrationsuction filtered, whereupon the crystals
  2. customwere dried

Sources & evidence

ORD record
ord-4ad7654aef7c4dfca523b660c5570aea
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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