Potassium Carbonate → HCID 15611948, Verbindung

HRID 357486

Reaktionsgleichung

Reaktionsgleichung von HRID 357486
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[OH:12][C:13]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16].CS([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][O:10][C:4]1[CH:5]=[C:6]([O:8][CH3:9])[N:7]=[C:2]([O:12][C:13]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:14]=2[C:15]([O:17][CH3:18])=[O:16])[N:3]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 31835Benzoic acid, 2-hydroxy-3-methyl-, methyl esterHCID 2733271Sodium methanesulfinateHCID 51523232-Chloro-4,6-dimethoxypyrimidine

Produkt 1

HCID 15611948HCID 15611948, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4.38 g (25 mmol) of 2-chloro-4,6-dimethoxypyrimidine, 4.17 g (25.0 mmol) of methyl 2-hydroxy-3-methylbenzoate and 0.66 g (6.3 mmol) of sodium methanesulfinate were heated in the presence of 5.17 g (37.5 mmol) of potassium carbonate in 25 ml of N,N-dimethylformamide to 120° C. with stirring. After 8 hours, the solvent was removed in a rotary evaporator at 60° C./20 mbar. The residue was taken up in 30 ml of water and 30 ml of dichloromethane. After the organic phase had been separated off, the aqueous phase was again extracted with 20 ml of dichloromethane. The combined organic phases was washed with water, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica gel column (eluent hexane/ethyl acetate 4:1). The title product was obtained from the product fraction in a yield of 5.23 g (65.8 percent of theory) (GC content 96 percent). The melting point of the compound was 73.8° to 79.1° C. Other data concerning the title compound was:

Aufarbeitung

  1. customthe solvent was removed in a rotary evaporator at 60° C./20 mbar
  2. customAfter the organic phase had been separated off
  3. extractionthe aqueous phase was again extracted with 20 ml of dichloromethane
  4. washThe combined organic phases was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by chromatography on a silica gel column (eluent hexane/ethyl acetate 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-aefd827c51644e598e3a91380a52eda0
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840892

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