Aspirin → 2-Acetyloxybenzoic acid 6-(chloromethyl)-2methylpyridinyl ester

HRID 1866126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866126
[C:1]([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[Cl:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22]Cl)[N:17]=1>CN(C=O)C.C(OCC)C>[Cl:14][CH2:15][C:16]1[N:17]=[C:18]([CH3:22])[C:19]([O:8][C:7](=[O:9])[C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][C:1](=[O:3])[CH3:2])=[CH:20][CH:21]=1

Komponenten

5

Edukt 2

HCID 2244AspirinHCID 3166542,6-Bis(chloromethyl)pyridine

Produkt 1

HCID 688807642-Acetyloxybenzoic acid 6-(chloromethyl)-2methylpyridinyl esterAusbeute 59,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of acetylsalicylic acid (1.6 g, 8.88 mmoles) in N,N′-dimethylformamide (20 ml) and under stirring sodium ethylate (0.64 g, 8.88 mmoles) is added. After 30 minutes the obtained solution is added to a solution of 2,6-bis-(chloromethyl)pyridine (4.72 g, 26.81 mmoles) in N,N′-dimethylformamide (20 ml). The solution is left at room temperature for 7 days, under stirring, then it is diluted with ethyl ether and washed with water. The separated organic phases are anhydrified with sodium sulphate and the solvent is evaporated at a reduced pressure. The reaction raw product is purified by chromatography on silica gel eluting with n-hexane/ethyl acetate 7/3. 1.7 g of the product as yellow oil are obtained.

Aufarbeitung

  1. washwashed with water
  2. customthe solvent is evaporated at a reduced pressure
  3. customThe reaction raw product
  4. customis purified by chromatography on silica gel eluting with n-hexane/ethyl acetate 7/3

Quellen und Nachweise

ORD-Eintrag
ord-a6f008d8cf7f40479d062c5b4a69b1bf
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629368B2

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