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

HRID 1724088

Reaction equation

HRID 1724088 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-0aced62d3bda4e49aa263edc42c1b467
Source dataset
uspto-grants-2009_02
Patent number
US07485723B2

Linked notes

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