Pyridine → N-[3-(1,3-dioxolan-2-yl)phenyl]acetamide

HRID 852880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852880
[C:1](Cl)(=[O:3])[CH3:2].[O:5]1[CH2:9][CH2:8][O:7][CH:6]1[C:10]1[CH:11]=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=1.N1C=CC=CC=1>C(Cl)Cl>[O:5]1[CH2:9][CH2:8][O:7][CH:6]1[C:10]1[CH:11]=[C:12]([NH:16][C:1](=[O:3])[CH3:2])[CH:13]=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 70203623-(1,3-Dioxolan-2-yl)aniline

Produkt 1

HCID 13987600N-[3-(1,3-dioxolan-2-yl)phenyl]acetamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of acetyl chloride (3.75 g, 0.048 mol, 3.4 mL) in CH2Cl2 (6.5 mL) was added dropwise over 15 min to an ice-bath chilled solution of 3-[1,3]dioxolan-2-yl-phenylamine (7.18 g, 0.043 mol) and pyridine (3.40 g, 0.043 mol, 3.5 mL) in CH2Cl2 (85 mL). The solution was then brought to room temperature, stirred for 1 hr, and poured onto ice-water (60 mL). The phases were separated, and the organic layer washed with water, saturated NaHCO3, brine and dried with MgSO4. Removal of the solvent in vacuo afforded N-(3-[1,3]dioxolan-2-yl-phenyl)-acetamide (8.01 g, 90%). 1H NMR (CDCl3) δ 2.08 (s, 3H), 4.03 (d of mult., ethylenedioxy), 5.71 (s, 1H), 7.17 (d, J=8 Hz, 1H), 7.26 (t, J=8 Hz, 1H), 7.53 (d, J=8 Hz, 1H), 7.62 (s, 1H), 8.32 (br s, 1H). 13C NMR (CDCl3) δ 168.9, 138.8, 138.3, 129.1, 122.3, 120.8, 118.1, 103.5, 65.4, 24.4.

Aufarbeitung

  1. customwas then brought to room temperature
  2. additionpoured onto ice-water (60 mL)
  3. customThe phases were separated
  4. washthe organic layer washed with water, saturated NaHCO3, brine
  5. dry with materialdried with MgSO4
  6. customRemoval of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-98bfe28740a342d1a04ae314a1a2da0c
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253194B2

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