Cyanuric chloride → 2-[cyanomethyl-(4,6-dichloro-1,3,5-triazin-2-yl)amino]acetonitrile

HRID 268154Notes

Reaction equation

HRID 268154 reaction equation
[NH:1]([CH2:5][C:6]#[N:7])[CH2:2][C:3]#[N:4].[N:8]1[C:15]([Cl:16])=[N:14][C:12](Cl)=[N:11][C:9]=1[Cl:10]>O1CCOCC1>[Cl:10][C:9]1[N:8]=[C:15]([Cl:16])[N:14]=[C:12]([N:1]([CH2:5][C:6]#[N:7])[CH2:2][C:3]#[N:4])[N:11]=1

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 69413Iminodiacetonitrile

Product 1

HCID 3527282-[cyanomethyl-(4,6-dichloro-1,3,5-triazin-2-yl)amino]acetonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

A solution of 9.5 g. (0.1 mole) of iminodiacetonitrile in 100 ml. dioxane was added to a stirred solution of 9.2 g. (0.05 mole) of cyanuric chloride in 100 ml. dioxane. The suspension was stirred at ambient temperature for 1 hour. An additional 100 ml. dioxane was added and mixture heated to 50°C. for 1 hour and filtered. The filtrate was diluted with 500 ml. ice/water and the solid filtered and dried to give 9.6 g. (80% yield), m.p. 154°-158°C.

Workup

  1. temperaturemixture heated to 50°C. for 1 hour
  2. filtrationfiltered
  3. additionThe filtrate was diluted with 500 ml
  4. filtrationice/water and the solid filtered
  5. customdried
  6. customto give 9.6 g

Sources & evidence

ORD record
ord-e757364905834a30ac118b4dd4a41fcb
Source dataset
uspto-grants-1976_03
Patent number
US03947374

Reaction notes

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