Sulfuric Acid → 1,3,5-Triazine, 2-chloro-4,6-bis(2,4-dimethylphenyl)-

HRID 50415

Reaction equation

HRID 50415 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[Al+3].[Cl-].[Cl-].[Cl-].OS(O)(=O)=O.[C:19]1([CH3:26])[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1>ClC1C=CC=CC=1>[Cl:3][C:2]1[N:4]=[C:5]([C:24]2[CH:23]=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[N:7]=[C:8]([C:24]2[CH:23]=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[N:1]=1.[CH3:26][C:19]1[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][C:24]=1[C:2]1[N:4]=[C:5]([C:24]2[CH:23]=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[N:7]=[C:8]([C:24]2[CH:23]=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[N:1]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7929M-XyleneHCID 7954Cyanuric chlorideHCID 6451240Aluminum(III) Chloride

Product 2

HCID 710591,3,5-Triazine, 2-chloro-4,6-bis(2,4-dimethylphenyl)-HCID 224759882,4,6-Tris(2,4-dimethylphenyl)-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a stirring mixture of 1 eq of cyanuric chloride, 3 eq of AlCl3 in chlorobenzene, was added 0.24 eq of concentrated H2SO4 at ice-bath temperature. After 5 min of stirring 2 eq of m-xylene was added. After another 5 min, the cooling bath was removed and the reaction mixture was stirred at room temperature. HPLC analysis after 2 h at room temperature showed 100% of the cyanuric chloride had reacted to give 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine and 2,4,6-tris(2,4-dimethylphenyl)-1,3,5-triazine, which were present in a ratio of 86:14.

Workup

  1. additionwas added
  2. customthe cooling bath was removed
  3. waitHPLC analysis after 2 h at room temperature showed
  4. custom100% of the cyanuric chloride had reacted

Sources & evidence

ORD record
ord-b5368d3525d64045b8a724b3abbc8513
Source dataset
uspto-grants-2004_03
Patent number
US06710177B2

Linked notes

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