Dimethyl Sulfoxide → Benzaldehyde, 2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-

HRID 704293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 704293
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[CH:12]1[CH:17]=[C:16]([CH:18]=[O:19])[C:15]([OH:20])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[CH3:11][O:10][C:4]1[CH:5]=[C:6]([O:8][CH3:9])[N:7]=[C:2]([O:20][C:15]2[CH:14]=[CH:13][CH:12]=[CH:17][C:16]=2[CH:18]=[O:19])[N:3]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 51523232-Chloro-4,6-dimethoxypyrimidine

Produkt 1

HCID 820623Benzaldehyde, 2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-Ausbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A 500-ml four-necked flask was charged with a mixture of 105 g (0.6 mole) of 2-chloro-4,6-dimethoxypyrimidine, 79.4 g (0.65 mole) of salicylic aldehyde 48.3 g (0.35 mole) of potassium carbonate and 450 ml of dimethylsulfoxide. The mixture was gradually heated, and stirred at 120° C. for 3 hours. After the reaction mixture was cooled, it was poured into 2 l of water. Through the procedures of benzene extraction, washing with water, drying over anhydrous sodium sulfate and concentration, 156 g of the target product were obtained as a crude oil. It was purified further by silica gel chromatography to obtain 117.1 g of white crystals (yield: 75.0%).

Aufarbeitung

  1. temperatureThe mixture was gradually heated
  2. temperatureAfter the reaction mixture was cooled
  3. extractionThrough the procedures of benzene extraction
  4. washwashing with water
  5. dry with materialdrying over anhydrous sodium sulfate and concentration

Quellen und Nachweise

ORD-Eintrag
ord-e989cb10e26d4c8bbe8ac96f0db85881
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04986846

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