Cyanuric chloride → HCID 53987106, compound

HRID 1657348Notes

Reaction equation

HRID 1657348 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[C:10]1([NH:16][C:17]#[N:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Na]>O1CCOCC1.O>[C:17]([N:16]([C:2]1[N:4]=[C:5]([N:16]([C:17]#[N:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=[C:8]([N:16]([C:17]#[N:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:1]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)#[N:18]

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 86733498HCID 86733498, compound

Product 1

HCID 53987106HCID 53987106, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 9.20g (0.05 mole) of cyanuric chloride in 100 ml of dioxane was added to 100 ml of ice water. To this mixture at room temperature was added dropwise a solution of 0.15 mole of sodium phenylcyanamide in 70 ml of water over a 30 minute period. After stirring for 3 hours at room temperature, the reaction mixture was refluxed for 16 hours. After cooling to room temperature the reaction mixture was filtered. The residue was washed with water and dried to give 17.2g (80%) of of TNCT, m.p. 209°-215°. Recrystallization from toluene gave 10.8g with an m.p. of 215°-218°.

Workup

  1. temperaturethe reaction mixture was refluxed for 16 hours
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. filtrationwas filtered
  4. washThe residue was washed with water
  5. customdried
  6. customto give 17.2g (80%) of of TNCT, m.p. 209°-215°
  7. customRecrystallization from toluene
  8. customgave 10.8g with an m.p. of 215°-218°

Sources & evidence

ORD record
ord-89ff46dd27154091a2f4a74e45ea4b7c
Source dataset
uspto-grants-1976_06
Patent number
US03960783

Reaction notes

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