2,4-Dimethylphenylisocyanide → 5-(2,4-Dimethylphenyl)-3-methyl-1-(2-pyridyl)-1,3,5-triazapenta-1,4-diene

HRID 2052721Notes

Reaction equation

HRID 2052721 reaction equation
[CH3:1][NH:2][CH:3]=[N:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[CH3:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[N+:19]#[C-:20]>C1(C)C=CC=CC=1>[CH3:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[N:19]=[CH:20][N:2]([CH3:1])[CH:3]=[N:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 42121842,4-DimethylphenylisocyanideHCID 178484920N-methyl-N'-(2-pyridyl)-formamidine

Product 1

HCID 544831495-(2,4-Dimethylphenyl)-3-methyl-1-(2-pyridyl)-1,3,5-triazapenta-1,4-dieneYield 20.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-methyl-N'-(2-pyridyl)-formamidine (2.5 g, 0.0185 m), 2,4-dimethylphenylisocyanide (2.4 g, 0.0185 m), cuprous oxide (trace amount) and dry toluene (60 ml) was heated on a steam bath with occasional agitation for 4 hours. The reaction mixture was then cooled, filtered through "Hyflo" (diatomaceous earth) and alumina, and the toluene filtrate evaporated to dryness in vacuo to yield a viscous oil. The oil was triturated with 60°-80° petroleum ether to yield a white solid. Crystallisation of this solid from ether/60°-80° petroleum ether yielded the product, 5-(2,4-dimethylphenyl)-3-methyl-1-(2-pyridyl)-1,3,5-triazapenta-1,4-diene, (1.0 g) m.p. 100°.

Workup

  1. temperaturewas heated on a steam bath with occasional agitation for 4 hours
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered through "Hyflo" (diatomaceous earth) and alumina
  4. customthe toluene filtrate evaporated to dryness in vacuo
  5. customto yield a viscous oil
  6. customThe oil was triturated with 60°-80° petroleum ether
  7. customto yield a white solid
  8. customCrystallisation of this solid from ether/60°-80° petroleum ether

Sources & evidence

ORD record
ord-e54e4d7aad5340f0b55d40c01b885dc1
Source dataset
uspto-grants-1980_01
Patent number
US04186264

Reaction notes

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