Sodium hydride → 8-nitro-1-[(diisopropylamino)methyl]-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

HRID 436574Notes

Reaction equation

HRID 436574 reaction equation
[CH:1]([N:4]([CH:6]([CH3:8])[CH3:7])O)([CH3:3])[CH3:2].[H-].[Na+].[N+:11]([C:14]1[CH:15]=[CH:16][C:17]2[N:23]3[C:24]([CH2:27]Cl)=[N:25][N:26]=[C:22]3[CH2:21][N:20]=[C:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[C:18]=2[CH:36]=1)([O-:13])=[O:12]>CN(C)C=O>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]2[N:23]3[C:24]([CH2:27][N:4]([CH:6]([CH3:8])[CH3:7])[CH:1]([CH3:3])[CH3:2])=[N:25][N:26]=[C:22]3[CH2:21][N:20]=[C:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[C:18]=2[CH:36]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5255450N,N-diisopropylhydroxylamineHCID 233374678-nitro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 233374688-nitro-1-[(diisopropylamino)methyl]-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In the manner given in Example 16, a solution of N,N-diisopropylhydroxylamine in dimethylformamide is treated with sodium hydride suspended in mineral oil, and the mixture is treated with 8-nitro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]-benzodiazepine to give 8-nitro-1-[(diisopropylamino)methyl]-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine, N1 -oxide.

Sources & evidence

ORD record
ord-3503b1ee74c6445b8e417e981d2e461e
Source dataset
uspto-grants-1977_02
Patent number
US04009175

Reaction notes

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