Pyridine → 1,3,5-Benzenetricarbonitrile, 2,4,6-trimethyl-

HRID 855472Notes

Reaction equation

HRID 855472 reaction equation
[C:1]([Cu])#[N:2].[N:4]1[CH:9]=CC=CC=1.Br[C:11]1[C:16]([CH3:17])=[C:15](Br)[C:14]([CH3:19])=[C:13](Br)[C:12]=1[CH3:21].[CH2:22](N)[NH2:23]>>[C:22]([C:11]1[C:16]([CH3:17])=[C:15]([C:9]#[N:4])[C:14]([CH3:19])=[C:13]([C:1]#[N:2])[C:12]=1[CH3:21])#[N:23]

Participants

5

Reactant 4

HCID 1049PyridineHCID 75408MethanediamineHCID 2629821,3,5-tribromo-2,4,6-trimethylbenzeneHCID 178418546HCID 178418546, compound

Product 1

HCID 1210551,3,5-Benzenetricarbonitrile, 2,4,6-trimethyl-

Procedure

CuCN (220 g, 243 mmol) and pyridine (146.7 g, 1.85 mol) were added to a high pressure reaction vessel, and well mixed, and then 2,4,6-tribromo-1,3,5-trimethylbenzene(25 g, 75.8 mmol) was added thereto. The reaction mixture was reacted at 205° C. for 2 hours. Cu therein was excluded with excessive methylene diamine, and then filtered by MC. Water in the reaction mixture was eliminated over MgSO4, and then solvent therein was evaporated in vacuum. The residue was absorbed to silica gel column and separated with a tube chromatography (Hx:MC=3:1) to obtain white solid [yield : 6 g (40.59%)].

Workup

  1. additionwell mixed
  2. customThe reaction mixture was reacted at 205° C. for 2 hours
  3. filtrationfiltered by MC
  4. customsolvent therein was evaporated in vacuum
  5. customThe residue was absorbed to silica gel column
  6. customseparated with a tube chromatography (Hx:MC=3:1)
  7. customto obtain white solid [yield : 6 g (40.59%)]

Sources & evidence

ORD record
ord-9586d76a007b444bb8c2bafbcc20e156
Source dataset
uspto-grants-2007_08
Patent number
US07261952B2

Reaction notes

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