Dimethylamine → HCID 12404532, compound

HRID 1763375Notes

Reaction equation

HRID 1763375 reaction equation
[C-]#N.[Na+].[CH3:4][NH:5][CH3:6].[C:7]1([C:13]2[C:19]3[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=3[N:17]3[N:25]=[C:26]([CH:28]=[O:29])[N:27]=[C:16]3[CH2:15][N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)(C)C.O1CCOCC1.[O-2].[O-2].[Mn+4]>[CH3:4][N:5]([CH3:6])[C:28]([C:26]1[N:27]=[C:16]2[CH2:15][N:14]=[C:13]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:19]3[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=3[N:17]2[N:25]=1)=[O:29]

Participants

7

Reactant 3

HCID 674DimethylamineHCID 8929Sodium CyanideHCID 20309862HCID 20309862, compound

Product 1

HCID 12404532HCID 12404532, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

2.94 g (0.06 mole) of sodium cyanide is suspended in 100 ml of isopropanol, and 50 ml of a 20% solution of dimethylamine in dioxane added at 0°-5° to the suspension. After 10 minutes, a solution of 4 g (0.0124 mole) of 6-phenyl-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodiazepine-2-carboxaldehyde in 50 ml of dioxane is quickly added dropwise, and, after a further 10 minutes, an addition made in two portions of 20.8 g of active manganese dioxide. The whole is stirred for a further 3 hours at 5°, filtered, and the filtrate concentrated in vacuo. After recrystallisation from methylene chloride/hexane, N,N-dimethyl-6-phenyl-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodiazepine-2-carboxamide is obtained, M.P. 135°-137°.

Workup

  1. waitafter a further 10 minutes
  2. additionan addition
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. customAfter recrystallisation from methylene chloride/hexane

Sources & evidence

ORD record
ord-99773e9e39c54d7eb249892dc489ed87
Source dataset
uspto-grants-1978_09
Patent number
US04111950

Reaction notes

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