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2-Naphthylamine → 3-[3-(Naphthalen-2-ylsulfamoyl)-phenyl]-acrylic acid methyl ester

HRID 351061
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 351061
[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](Cl)(=[O:14])=[O:13])[CH:7]=1.[NH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.O>[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](=[O:14])(=[O:13])[NH:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 70572-NaphthylamineHCID 516892Sodium BicarbonateHCID 737087423-(3-Chlorosulfonylphenyl)acrylic acid methyl ester

Produkt 1

HCID 670194963-[3-(Naphthalen-2-ylsulfamoyl)-phenyl]-acrylic acid methyl esterAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 31275
1,4-Dioxane
Lösungsmittel

Versuchsvorschrift

A solution of 3-(3-chlorosulfonylphenyl)acrylic acid methyl ester (3) (1.0 g, 3.83 mmol) in dioxane (10 ml) was added to a mixture of 2-aminonaphthalene (0.55 g, 3.83 mmol) and NaHCO3 (0.48 g, 5.71 mmol) in water (6 ml), and the resultant solution was stirred at room temperature until the completion of the reaction (control by TLC). The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was chromatographed on silica gel with petroleum ether-ethyl acetate (3:2, v/v) as eluent. The obtained product was crystallised from petroleum ether-ethyl acetate to give the title compound (0.52 g, 34%) as a white solid. 1H NMR (DMSO-d6, HMDSO), 6:3.73 (3H, s); 6.67 (1H, d, J=16.0 Hz); 7.21–8.07 (11H, m); 8.16 (1H, s); 10.55 (1H, s).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 2N HCl
  3. washThe organic layer was washed successively with water, saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed
  6. customthe residue was chromatographed on silica gel with petroleum ether-ethyl acetate (3:2
  7. customThe obtained product was crystallised from petroleum ether-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4f656cc6e3e647c0b90f3a9f34103541
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07183298B2

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