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

HRID 1378144Notes

Reaction equation

HRID 1378144 reaction equation
[Cl: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.Cl.[NH2:22][OH:23].[Na].CO>O>[Cl: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:22][OH:23])[NH2:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 53905765(S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile

Product 1

HCID 54137540(S)-8-chloro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoximeYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

178.7 g (628 mmol) of (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carbonitrile and 65.5 g (941 mmol) of hydroxylamine hydrochloride were added to a solution prepared from 17.3 g (753 mmol) of sodium and 1.5 l of methanol. The reaction mixture was stirred at room temperature overnight and subsequently diluted with 1 l of water. The suspension obtained was suction filtered and the crystals were dried. There were obtained 169.7 g (85%) of (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carboxamidoxime of decomposition point 269°.

Workup

  1. customThe suspension obtained
  2. filtrationfiltered
  3. customthe crystals were dried

Sources & evidence

ORD record
ord-6ca02ebe251e49cb8f34c58625bb573e
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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