2,4,6-Trimethylphenol → 4-Chloro-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)-pyrimidine

HRID 968025

Reaktionsgleichung

Reaktionsgleichung von HRID 968025
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[H-].[Na+].[CH3:13][C:14]1[N:19]=[C:18](Cl)[C:17]([CH3:21])=[C:16]([Cl:22])[N:15]=1>C1COCC1>[Cl:22][C:16]1[C:17]([CH3:21])=[C:18]([O:10][C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])[N:19]=[C:14]([CH3:13])[N:15]=1

Komponenten

5

Edukt 3

HCID 106982,4,6-TrimethylphenolHCID 24758Sodium hydrideHCID 2370134,6-Dichloro-2,5-dimethylpyrimidine

Produkt 1

HCID 219120504-Chloro-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)-pyrimidineAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2,4,6-trimethylphenol (2.720 g, 20 mmol) in 60 ml of dry THF was treated with NaH (60% in oil, 1,200 g, 30 mmol) at room temperature. After stirring at room temperature for 15 minutes, 2,5-dimethyl-4,6-dichloropyrimidine (3.34 g, 20 mmol) was added and the resulting mixture was heated at reflux for 15 hours. The mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was dried and concentrated to give 5.4528 g of beige solid. The solid was recrystallized from isopropanol to give 5.1345 g of pale yellow solid. mp 86-87° C.; high MS (C15H17ClN20) calc. 276.1025, found 276.10359. 1H NMR (CDCl3) δ 6.87 (s, 2H), 2.37 (s, 6H), 2.28 (s, 3H), 2.01 (s, 6H) ppm.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 15 hours
  3. customThe mixture was quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d04091c0d33b4d3d9d3242718af895d2
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956047B1

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