Formaldehyde → 1-[2-(dimethylamino)ethyl]-8-chloro-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

HRID 1731086Notes

Reaction equation

HRID 1731086 reaction equation
N[CH2:2][CH2:3][C:4]1[N:8]2[C:9]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:10]=3[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])=[N:12][CH2:13][C:7]2=[N:6][N:5]=1.C=O.[C:28]([BH3-])#[N:29].[Na+].[CH2:32](N)CN>C(#N)C.C(O)(=O)C>[CH3:32][N:29]([CH3:28])[CH2:2][CH2:3][C:4]1[N:8]2[C:9]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:10]=3[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])=[N:12][CH2:13][C:7]2=[N:6][N:5]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 3301EthylenediamineHCID 5003444Sodium cyanoborohydrideHCID 126124071-(2-aminoethyl)-8-chloro-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 126124171-[2-(dimethylamino)ethyl]-8-chloro-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

In the manner given in Example 22, a mixture of 1-(2-aminoethyl)-8-chloro-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine, 37% aqueous formaldehyde and acetic acid in acetonitrile is treated with sodium cyanoborohydride and the resulting boron complex is warmed with aqueous ethylenediamine to give 1-[2-(dimethylamino)ethyl]-8-chloro-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine.

Sources & evidence

ORD record
ord-9155c388f8c64c8abbdc4a52a7e33a68
Source dataset
uspto-grants-1976_11
Patent number
US03994941

Reaction notes

Loading…