Cyanuric chloride → HCID 20429677, compound

HRID 325753Notes

Reaction equation

HRID 325753 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[C:10]1([Mg]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH2:18][C:19]1[CH:20]=[C:21]([C:25]#[CH:26])[CH:22]=[CH:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl.O>[C:10]1([C:2]2[N:4]=[C:5]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[CH:26])[CH:20]=3)[N:7]=[C:8]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[CH:26])[CH:20]=3)[N:1]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 7954Cyanuric chlorideHCID 11430Potassium CarbonateHCID 104682Benzenamine, 3-ethynyl-HCID 178418255HCID 178418255, compound

Product 1

HCID 20429677HCID 20429677, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

One mole of cyanuric chloride was treated with phenylmagnesium bromide as described in Step I of Example I. The resulting reaction product (10.0 g, 0.044 mole) in CHCl3 (100 ml) was stirred in a 250 ml 3-neck round bottom flask while m-aminophenylacetylene (10.5 g, 0.09 mole) was added dropwise with cooling. To this mixture was added K2CO3 (12.4 g, 0.09 mole) and water (20 ml). The organic layer was separated, dried, and the solvent evaporated. The residue was triturated in benzene and dried to give 6-phenyl-2,4-bis(3-ethynylphenylamino)-s-triazine a compound that melted at 210° C. with polymerization. Thermo-gravimetric analysis showed that the polymer was stable to 425° C.

Workup

  1. additionwas added dropwise
  2. temperaturewith cooling
  3. customThe organic layer was separated
  4. customdried
  5. customthe solvent evaporated
  6. customThe residue was triturated in benzene
  7. customdried

Sources & evidence

ORD record
ord-865361605b6b473b97436e5841037f59
Source dataset
uspto-grants-1984_04
Patent number
US04442278

Reaction notes

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