Hydrochloric Acid → 1,3,5-Triazine, 2-chloro-4,6-bis(2,4-dimethylphenyl)-

HRID 50414

Reaktionsgleichung

Reaktionsgleichung von HRID 50414
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[Al+3].[Cl-].[Cl-].[Cl-].[C:14]1([CH3:21])[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1.Cl>ClC1C=CC=CC=1>[Cl:3][C:2]1[N:4]=[C:5]([C:19]2[CH:18]=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[N:7]=[C:8]([C:19]2[CH:18]=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[N:1]=1.[CH3:21][C:14]1[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][C:19]=1[C:2]1[N:4]=[C:5]([C:19]2[CH:18]=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[N:7]=[C:8]([C:19]2[CH:18]=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[N:1]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7929M-XyleneHCID 7954Cyanuric chloride3×HCID 6451240Aluminum(III) Chloride

Produkt 2

HCID 710591,3,5-Triazine, 2-chloro-4,6-bis(2,4-dimethylphenyl)-HCID 224759882,4,6-Tris(2,4-dimethylphenyl)-1,3,5-triazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

To a stirring mixture of 1 eq of cyanuric chloride, 3 eq of AlCl3, and 1.9 eq of m-xylene in chlorobenzene, was added 13% (based on the weight of cyanuric chloride) of concentrated HCl at ice-bath temperature. Within 30 min at room temperature, 97% of the cyanuric chloride had reacted, to produce 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine and 2,4,6-tris(2,4-dimethylphenyl)-1,3,5-triazine in a ratio of 96:4; no side products were detected. Further stirring gave 99.5% cyanuric chloride conversion, with the ratio of 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine to 2,4,6-tris(2,4-dimethylphenyl)-1,3,5-triazine unchanged and no other products were detected. Thereafter, the reaction mixture was allowed to react with 1.1 eq of resorcinol at 85° C. for 1.5 h. HPLC analysis of the reaction mixture showed the formation of 92.7% 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 5% 2,4,6-tris(2,4-dimethylphenyl)-1,3,5-triazine, and 2.3% unreacted 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine.

Aufarbeitung

  1. additionwas added 13% (

Quellen und Nachweise

ORD-Eintrag
ord-f67882ff092a4fcc8d68dc3a0bb4530b
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710177B2

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