Cyanuric chloride → 4,6-Dichloro-N-(4-ethenylphenyl)-1,3,5-triazin-2-amine

HRID 1863358Notes

Reaction equation

HRID 1863358 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.[CH:10]([C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1)=[CH2:11].C(N(CC)C(C)C)(C)C>CC(C)=O>[CH:10]([C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:2]2[N:1]=[C:8]([Cl:9])[N:7]=[C:5]([Cl:6])[N:4]=2)=[CH:14][CH:13]=1)=[CH2:11]

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 737004-AminostyreneHCID 81531Diisopropylethylamine

Product 1

HCID 203375874,6-Dichloro-N-(4-ethenylphenyl)-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 18.4 g. (0.1 mole) of cyanuric chloride in 150 ml. of acetone being stirred at 0°-5° C. was added dropwise over a 1/2 hr. period a solution of 11.9 g. (0.1 mole) of 4-vinylaniline and 12.9 g. (0.1 mole) of N,N-di-iso-propylethylamine. After the addition was complete, the solution was stirred at room temperature for 15 min., and then poured into 1 liter of ice water to isolate the product. The product was collected by filtration, washed with 200 ml. of water, and dried in vacuo at room temperature to give 25 g. Recrystallization from 75 ml. of benzene gave 15.0 g. (56%) (mp 152°-154°).

Workup

  1. additionwas added dropwise over a 1/2 hr
  2. additionAfter the addition
  3. customto isolate the product
  4. filtrationThe product was collected by filtration
  5. washwashed with 200 ml
  6. dry with materialof water, and dried in vacuo at room temperature
  7. customto give 25 g
  8. customRecrystallization from 75 ml
  9. customof benzene gave 15.0 g

Sources & evidence

ORD record
ord-511d1d62c08440b78236c33151afd931
Source dataset
uspto-grants-1979_09
Patent number
US04168976

Reaction notes

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