Acetic Anhydride → N-(2,3-dihydro-1,4-benzodioxin-5-yl)acetamide

HRID 1487200

Reaktionsgleichung

Reaktionsgleichung von HRID 1487200
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[C:7]([NH2:11])=[CH:8][CH:9]=[CH:10][C:2]1=2.[C:12](OC(=O)C)(=[O:14])[CH3:13]>C(O)C>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=[CH:10][C:2]1=2

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 117883872,3-Dihydro-1,4-benzodioxin-5-amine2×

Produkt 1

HCID 658593N-(2,3-dihydro-1,4-benzodioxin-5-yl)acetamideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2,3-dihydrobenzo[b][1,4]dioxin-5-amine (Intermediate B3, 4.5 g, 30 mmol) in ethanol (50 mL) at room temperature was slowly added acetic anhydride (3.0 g, 30 mmol). After the addition was over, the mixture was stirred at room temperature for 5 minutes. The resulting suspension was concentrated to give the crude product, which was purified by silica gel column chromatography (petroleum ether/ethyl acetate 4/1) to afford the product N-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acetamide (5.5 g, yield 95%). 1H NMR (400 MHz, CDCl3) δ ppm 9.12 (s, 1H), 7.44-7.46 (d, 1H, J=8.0 Hz), 6.71-6.75 (t, 1H, J=8.0 Hz), 6.59-6.61 (d, 1H, J=7.6 Hz), 4.23-4.30 (m, 4H), 2.06 (s, 3H).

Aufarbeitung

  1. customat room temperature
  2. additionAfter the addition
  3. concentrationThe resulting suspension was concentrated
  4. customto give the crude product, which
  5. customwas purified by silica gel column chromatography (petroleum ether/ethyl acetate 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-aad21df284a645318e6f503c791ea2df
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428508B2

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