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

HRID 268537Notes

Reaction equation

HRID 268537 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[C:14]([CH2:17]N)=[N:15][N:16]=[C:12]3[CH2:11][N:10]=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[C:8]=2[CH:26]=1)([O-:3])=[O:2].C=O.[C:29]([BH3-])#[N:30].[Na+].[C:33](O)(=O)CC>C(#N)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[C:14]([CH2:17][N:30]([CH3:29])[CH3:33])=[N:15][N:16]=[C:12]3[CH2:11][N:10]=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[C:8]=2[CH:26]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1032Propionic AcidHCID 5003444Sodium cyanoborohydrideHCID 215518878-Nitro-1-(aminomethyl)-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 6342AcetonitrileSolvent

Procedure

In the manner given in Example 23 a solution of 8-nitro-1-(aminomethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine in acetonitrile is treated with formalin, sodium cyanoborohydride and propionic acid to give 8-nitro-1-[ (dimethylamino)methyl]-6-(o-chlorophenyl)4H-s-triazolo[4,3-a][1,4]benzodiazepine.

Sources & evidence

ORD record
ord-a25171d2c1f944f6a9f76a3e5d9368cc
Source dataset
uspto-grants-1976_03
Patent number
US03947466

Reaction notes

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