Acetyl chloride → 2-Phenoxyacetanilide

HRID 1750914

Reaktionsgleichung

Reaktionsgleichung von HRID 1750914
[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23]>ClCCl>[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH:10][C:22](=[O:24])[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 75899Benzenamine, 2-phenoxy-

Produkt 1

HCID 8970802-PhenoxyacetanilideAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The mixture of 2-phenoxyaniline (100 g, 540 mmol), triethylamine (0.090 L, 648 mmol) and 1 L dichloromethane was cooled to 0° C. by ice bath. Acetyl chloride (0.04 L, 567 mmol) was added dropwise. After the addition completed, the reaction was stirred under room temperature for 2 h. The mixture was concentrated and diluted by dichloromethane. The organic phase was washed by water and dried over sodium sulfate. The crude product was purified by silica gel column (20% EtOAc in hexane) to give red brown oily solid N-(2-phenoxyphenyl)acetamide (120 g, 98% yield).

Aufarbeitung

  1. additionAfter the addition
  2. concentrationThe mixture was concentrated
  3. additiondiluted by dichloromethane
  4. washThe organic phase was washed by water
  5. dry with materialdried over sodium sulfate
  6. customThe crude product was purified by silica gel column (20% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1404d205651c425bac288e7484b73921
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156870B2

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