M-Xylene → 1,3,5-Triazine, 2-chloro-4,6-bis(2,4-dimethylphenyl)-

Reaction equation

[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[C:10]1([CH3:17])[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=1>>[Cl:3][C:2]1[N:4]=[C:5]([C:15]2[CH:14]=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[N:7]=[C:8]([C:15]2[CH:14]=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[N:1]=1

Participants

Reactant 2

HCID 7929M-Xylene

HCID 7954Cyanuric chloride

Product 1

HCID 710591,3,5-Triazine, 2-chloro-4,6-bis(2,4-dimethylphenyl)-

Procedure

The reaction of cyanuric chloride with 1,3-xylene under Friedel-Crafts conditions to give 2-chloro-4,6-bis(2,4-dimethylphenyl)-s-triazine is known, e.g. from DE-A-1 169 947 and Helv. Chim. Acta 55, 1589 (1972). However, the product can also be obtained using an appropriate Grignard reagent, such as described in Helv. Chim. Acta 33, 1365 (1950) and U.S. Pat. No. 4,092,466.

Sources & evidence

ORD record: ord-3d49ae6f297d47999ae3e523cd23084d
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05726310

Reaction notes

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