Acetic Anhydride → 2-(Benzo[b]thien-3-yl)ethyl acetamide

HRID 52020

Reaktionsgleichung

Reaktionsgleichung von HRID 52020
[S:1]1[CH:5]=[C:4]([CH2:6][CH2:7]N)[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[CH3:13][C:14]([O:16]C(C)=O)=O.CC[N:22](CC)CC>CN(C=O)C.O>[S:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:13][C:14]([NH2:22])=[O:16])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Komponenten

6

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 26743Benzo[b]thiophene-3-ethanamine

Produkt 1

HCID 571208502-(Benzo[b]thien-3-yl)ethyl acetamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(Benzo[b]thien-3-yl)ethylamine (0.75 g, 4.23 mmol) was dissolved in DMF (5 mL) and 5 equivalents of Ac2O and 3 equivalents of Et3N were added. The mixture was stirred for 18 h at room temperature, diluted with H2O (25 mL) and extracted with CH2Cl2 (2×25 mL). The organic extracts were dried over Na2SO4 and concentrated to a residue to provide 0.88 g (94%) of 4 as a viscous liquid. 1H NMR (CDCl3) δ1.88 (s, 3, --CH3), 3.00(m, 2, --CH2 --), 3.54 (m, 2, CH2 --NH), 6.29 (br s, 1, NH), 7.10 (s, 1, CH--S), 7.25-7.37 (m, 2, phenyl), 7.72-7.86 (m, 2, phenyl).

Aufarbeitung

  1. extractionextracted with CH2Cl2 (2×25 mL)
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. concentrationconcentrated to a residue

Quellen und Nachweise

ORD-Eintrag
ord-5bc35e0a9acf44bf947e48a2e443f1a6
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616575

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