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

HRID 1724085Notes

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-].S(=O)(=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

Conditions

Temperature: 10 °C

Procedure

To a stirring mixture of 1 eq of cyanuric chloride, 3.5 eq of AlCl3 in chlorobenzene, was added 0.036 eq of sulfuric acid as a 10% aq. solution at ice-bath temperature. After 10 min of stirring 1.9 eq of m-xylene was added. After 5 min at ice bath temperature the reaction mixture was allowed to warm to 10° C. After 1 h 20 min HPLC analysis showed 89% 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 89:11 HPLC analysis, after 3 h at 9-11° C., showed 94% 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 95:5. HPLC analysis, after 5 h at 9-11° C. and 17 h at room temperature, showed 98.5% 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 97:3.

Workup

additionwas added
waitAfter 1 h 20 min HPLC analysis showed

Sources & evidence

ORD record: ord-11f1e698f92d4190b11aea91222e6914
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485723B2

Reaction notes

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