Hydrochloric Acid → 2-Chloro-4,6-di-p-tolyl-1,3,5-triazine

HRID 1019301

Reaction equation

HRID 1019301 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[Cl-].[Al+3].[Cl-].[Cl-].Cl.[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClC1C=CC=CC=1Cl>[Cl:3][C:2]1[N:4]=[C:5]([C:18]2[CH:19]=[CH:20][C:15]([CH3:21])=[CH:16][CH:17]=2)[N:7]=[C:8]([C:18]2[CH:19]=[CH:20][C:15]([CH3:21])=[CH:16][CH:17]=2)[N:1]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 7954Cyanuric chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 308512-Chloro-4,6-di-p-tolyl-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To a stirring mixture of 1 eq of cyanuric chloride and 3 eq of aluminum chloride in o-dichlorobenzene at ice bath temperature was added concentrated HCl (13 wt % based on cyanuric chloride). After 10 minutes, 1.9 eq of toluene was added and the reaction mixture was stirred at ice bath temperature for 30 minutes. The cooling bath was removed, the reaction mixture was allowed to warm to room temperature, and stirred for 21 h. HPLC analysis indicated about 95% cyanuric chloride conversion to 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine and the isomer 2-chloro-4-(4-methylphenyl)-6-(2-methylphenyl)-1,3,5-triazine.

Workup

  1. customThe cooling bath was removed
  2. stirringstirred for 21 h

Sources & evidence

ORD record
ord-4937ccd740b941f9972c40a4442368b7
Source dataset
uspto-grants-2002_11
Patent number
US06486316B1

Linked notes

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