Dimethylamine → N,N-dimethyl-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine-1-carboxamide

HRID 1414907Notes

Reaction equation

HRID 1414907 reaction equation
C(O)(C)C.[CH3:5][NH:6][CH3:7].[C-]#N.[Na+].[C:11]1([C:17]2[C:23]3[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=3[N:21]3[C:29]([CH:32]=[O:33])=[N:30][N:31]=[C:20]3[CH2:19][N:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCOCC1.O1CCOCC1.C(O)(C)C.[O-2].[O-2].[Mn+4].C(Cl)Cl>[CH3:5][N:6]([CH3:7])[C:32]([C:29]1[N:21]2[C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[C:17]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[N:18][CH2:19][C:20]2=[N:31][N:30]=1)=[O:33]

Participants

9

Reactant 4

HCID 674DimethylamineHCID 3776IsopropanolHCID 8929Sodium CyanideHCID 214860116-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine-1-carboxaldehyde

Product 1

HCID 21486010N,N-dimethyl-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine-1-carboxamide

Reagents, catalysts & solvents 4

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolventHCID 20284604Dioxane isopropanolSolvent

Procedure

80 ml of isopropanol is added to 120 ml of a 20% solution of dimethylamine in dioxane. After this has cooled to 0°, additions are made, with stirring, of 3.7 g (0.075 mole) of sodium cyanide and, after 5 minutes, of a solution of 4.8 g (0.015 mole) of 6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine-1-carboxaldehyde [see Example 1 a)] in 50 ml of dioxane/isopropanol (1:1), as well as of 13 g of manganese dioxide. After 10 minutes, a further addition is made of 13 g of manganese dioxide (total 0.3 mole), and the mixture subsequently stirred for 4 hours at 0°. After the addition of methylene chloride, the reaction mixture is filtered and the filtrate concentrated by evaporation. Crystallisation of the residue from ethyl acetate/petroleum ether yields N,N-dimethyl-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine-1-carboxamide, M.P. 180°- 181° C.

Workup

  1. temperatureAfter this has cooled to 0°
  2. additiona further addition
  3. filtrationthe reaction mixture is filtered
  4. concentrationthe filtrate concentrated by evaporation
  5. customCrystallisation of the residue from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-184ac9eff0f74e0da193870791c5a6d7
Source dataset
uspto-grants-1977_01
Patent number
US04002764

Reaction notes

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