Diethylhydroxylamine → 8-bromo-1-[(diethylamino)methyl]-6-(2-pyridyl)-4H-s-triazolo [4,3-a][1,4]benzodiazepine

HRID 436575Notes

Reaction equation

HRID 436575 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15]Cl)=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:6]=2[CH:23]=1.[CH2:24]([N:26]([CH2:28][CH3:29])O)[CH3:25].[H-].[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15][N:26]([CH2:28][CH3:29])[CH2:24][CH3:25])=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 19463DiethylhydroxylamineHCID 24758Sodium hydrideHCID 203612008-bromo-1-(chloromethyl)-6-(2-pyridyl)-4H-s triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 203612248-bromo-1-[(diethylamino)methyl]-6-(2-pyridyl)-4H-s-triazolo [4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In the manner given in Example 15, 8-bromo-1-(chloromethyl)-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]-benzodiazepine is treated with a cold mixture of N,N-diethylhydroxylamine and sodium hydride in dimethylformamide to give 8-bromo-1-[(diethylamino)methyl]-6-(2-pyridyl)-4H-s-triazolo[4,3-a ][1,4]benzodiazepine, N1 -oxide.

Sources & evidence

ORD record
ord-a91e30b91c7a4f0da0dc97e997572a52
Source dataset
uspto-grants-1977_02
Patent number
US04009175

Reaction notes

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