1-Naphthaleneacetamide → 2-(naphthalen-1-yl)-N-(thiophen-3-yl)acetamide

HRID 1519970

Reaktionsgleichung

Reaktionsgleichung von HRID 1519970
[C:1]1([CH2:11][C:12]([NH2:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.I[C:16]1[CH:20]=[CH:19][S:18][CH:17]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C>[C:1]1([CH2:11][C:12]([NH:14][C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 4

HCID 68611-NaphthaleneacetamideHCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 663323-Iodothiophene

Produkt 1

HCID 687555152-(naphthalen-1-yl)-N-(thiophen-3-yl)acetamideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-(naphthalen-1-yl)acetamide (14.00 g, 75.6 mmol), 3-iodothiophene (10.15 g, 48.3 mmol), trans-1,2diaminocyclohexane (3.0 ml, 25.0 mmol), cuprous iodide (1.97 g, 10.3 mmol), and potassium carbonate (13.66 g, 98.8 mmol) in dioxane (50 ml) was placed into a preheated oil bath at 95° C. After stirring for 18 h, the heterogenous mixture was diluted with water and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was flash chromatographed with 19:1, 9:1, 17:3, and 4:1 methylene chloride:ethyl acetate as the eluant to yield 12.26 g (95% yield) of 2-(naphthalen-1-yl)-N-(thiophen-3-yl)acetamide as a brown solid. Method [7] Retention time 2.07 min by HPLC (MH+ 268).

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed with 19:1, 9:1, 17:3, and 4:1 methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-d70f4c51960e4296b3c756b18aa907f2
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073891B2

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