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

HRID 436572Notes

Reaction equation

HRID 436572 reaction equation
[CH3:1][N:2]([CH3:4])O.[H-].[Na+].[N+:7]([C:10]1[CH:11]=[CH:12][C:13]2[N:19]3[C:20]([CH2:23]Cl)=[N:21][N:22]=[C:18]3[CH2:17][N:16]=[C:15]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])[C:14]=2[CH:32]=1)([O-:9])=[O:8]>CN(C)C=O>[N+:7]([C:10]1[CH:11]=[CH:12][C:13]2[N:19]3[C:20]([CH2:23][N:2]([CH3:4])[CH3:1])=[N:21][N:22]=[C:18]3[CH2:17][N:16]=[C:15]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])[C:14]=2[CH:32]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27970DimethylhydroxylamineHCID 233374678-nitro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 202918451-[(dimethylamino)methyl]-8-nitro-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-dimethylhydroxylamine 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-[(dimethylamino)methyl]-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine, N1 -oxide.

Sources & evidence

ORD record
ord-f4e8a7e2981b4752bbba647fb449295f
Source dataset
uspto-grants-1977_02
Patent number
US04009175

Reaction notes

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