Hydrochloric Acid → HCID 22248020, Verbindung

HRID 914827

Reaktionsgleichung

Reaktionsgleichung von HRID 914827
C1(OP([CH:17](NC2C=CC=CC=2)[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)(=O)OC2C=CC=CC=2)C=CC=CC=1.[F:31][C:32]1[C:33]([CH:37]=O)=[CH:34][S:35][CH:36]=1.C(=O)([O-])[O-:40].[Cs+].[Cs+].Cl.[OH-].[Na+]>O1CCCC1CCCO>[F:31][C:32]1[C:33]([CH2:37][C:17]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[O:40])=[CH:34][S:35][CH:36]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 423769diphenyl (phenylamino)(pyridin-4-yl)methylphosphonateHCID 22247846614729-75-8

Produkt 1

HCID 22248020HCID 22248020, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 130202-Furanpropanol, tetrahydro-Lösungsmittel

Versuchsvorschrift

After dissolving 19.6 g of [(phenylamino)-(4-pyridylmethyl)]phosphonic acid diphenyl ester [CAS No. 3360-72-3] in 115 ml of tetrahydrofuran-2-propanol (4:1), 6.02 g of 4-fluorothiophene-3-carboxaldehyde and 19.61 g of anhydrous cesium carbonate were added and the mixture was stirred overnight at room temperature. Next, 90 ml of 5N hydrochloric acid was added to the reaction mixture and the mixture was stirred at room temperature for 6 hours. After adding a 5N sodium hydroxide solution to the reaction solution, extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate). The obtained solid was washed with n-hexane to obtain the title compound (3.66 g, 36% yield).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 6 hours
  2. extractionto the reaction solution, extraction
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)
  7. washThe obtained solid was washed with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-9da64ea8e8ed453aa3c20cca7b286d84
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265108B2

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