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

HRID 50413
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 50413
N1C(Cl)=NC(Cl)=NC=1Cl.[C:10]1([CH3:17])[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=1.[Al+3].[Cl-].[Cl-].[Cl-].C1(C=CC=C(O)C=1)O.[Cl:30][C:31]1[N:36]=[C:35]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][C:38]=2[CH3:44])[N:34]=[C:33]([C:45]2[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][C:46]=2[CH3:52])[N:32]=1>ClC1C=CC=CC=1>[Cl:30][C:31]1[N:32]=[C:33]([C:45]2[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][C:46]=2[CH3:52])[N:34]=[C:35]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][C:38]=2[CH3:44])[N:36]=1.[CH3:17][C:10]1[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][C:15]=1[C:31]1[N:36]=[C:35]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][C:38]=2[CH3:44])[N:34]=[C:33]([C:45]2[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][C:46]=2[CH3:52])[N:32]=1
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Komponenten

8

Edukt 5

HCID 5054ResorcinolHCID 7929M-XyleneHCID 7954Cyanuric chloride2×HCID 710591,3,5-Triazine, 2-chloro-4,6-bis(2,4-dimethylphenyl)-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

Cyanuric chloride was allowed to react with 2.05 eq of m-xylene, in the presence of 3 eq of AlCl3 and 0.2 of resorcinol, in chlorobenzene at 5° C. for 0.5 h and then at room temperature for 3 h. The first step (conversion to 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine) was completed in less than 16 h, with more than 98% cyanuric chloride conversion as determined by HPLC analysis. 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine and 2,4,6-tris(2,4-dimethylphenyl)-1,3,5-triazine were formed in an 86:14 ratio; no other products were detected. The reaction mixture was allowed to react with additional resorcinol at 110° C. for 1.5 h. HPLC analysis showed a product mixture of 82% 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 14% 2,4,6-tris(2,4-dimethylphenyl)-1,3,5-triazine, and 2% 2,4,6-tris(2,4-dihydroxyphenyl)-1,3,5-triazine, with only 1.5% unreacted 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine.

Quellen und Nachweise

ORD-Eintrag
ord-a98db76593b44ef79acd4d9ab98eb4ff
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06710177B2

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