Hydrochloric Acid → 1,3,5-Triazine, 2,4,6-tris(trichloromethyl)-

HRID 270622

Reaction equation

HRID 270622 reaction equation
[Cl:1][C:2]([Cl:6])([Cl:5])[C:3]#[N:4].[ClH:7]>>[Cl:1][C:2]([Cl:6])([Cl:5])[C:3]1[N:4]=[C:3]([C:2]([Cl:1])([Cl:7])[Cl:7])[N:4]=[C:3]([C:2]([Cl:6])([Cl:5])[Cl:1])[N:4]=1

Participants

3

Procedure

Aluminum bromide (0.5 g, 0.0019 mol) was added to a solution of the compound 5a (4.4 g, 0.019 mol) obtained in the above (1) dissolved in trichloroacetonitrile (43 g, 0.298 mol). Dry hydrogen chloride gas was passed through the reaction mixture at −10° C. for 2 hours. Then, the mixture was stirred at room temperature for one day. Trichloroacetonitrile was removed under reduced pressure. The residue was purified by a column (hexane/ethyl acetate=9/1). As a result, the mixture of 2,4-trichloromethyl-(2′-acetylbiphenyl)-6-triazine (5b) and 2,4,6-tris(trichloromethyl)-1,3,5-triazine was obtained. These two products were not separated since they have similar solubility in any solvent.

Workup

  1. customTrichloroacetonitrile was removed under reduced pressure
  2. customThe residue was purified by a column (hexane/ethyl acetate=9/1)
  3. additionAs a result, the mixture of 2,4-trichloromethyl-(2′-acetylbiphenyl)-6-triazine (5b)

Sources & evidence

ORD record
ord-3165f3a3ab614ac5ab032f5904dba123
Source dataset
uspto-grants-2008_11
Patent number
US07449574B2

Linked notes

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