Benzene → 2-Chloro-4,6-diphenyl-1,3,5-triazine

HRID 1019300Notes

Reaction equation

HRID 1019300 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.[CH:15]1[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:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:7]=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:1]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 7954Cyanuric chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 196982-Chloro-4,6-diphenyl-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, 1.95 eq of benzene was added and the reaction mixture stirred at ice bath temperature for 10 minutes. The cooling bath was removed, the reaction was allowed to warm to room temperature, and stirred. After 26 h at room temperature, an HPLC analysis indicated about 86% cyanuric chloride conversion to 2-chloro-2,6-bisphenyl-1,3,5-triazine. The stirring was continued for 24 h at room temperature. The HPLC analysis showed the cyanuric chloride conversion to 92% with >96% being 2-chloro-4,6-bisphenyl-1,3,5-triazine and less than 2% of 2,4,6-trisphenyl-1,3,5-triazine. The result was confirmed by LCMS.

Workup

  1. customThe cooling bath was removed
  2. stirringstirred
  3. waitAfter 26 h at room temperature
  4. waitThe stirring was continued for 24 h at room temperature

Sources & evidence

ORD record
ord-56a8208b8ca04937a5ddfd1f97a68c50
Source dataset
uspto-grants-2002_11
Patent number
US06486316B1

Reaction notes

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