Chloroacetyl chloride → Acetamide, N-(5-hydroxy-1-naphthalenyl)-

HRID 395225

Reaktionsgleichung

Reaktionsgleichung von HRID 395225
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[OH:12].C(=O)([O-])[O-].[Ca+2].Cl[CH2:19][C:20](Cl)=[O:21]>O1CCOCC1>[OH:12][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:8]=1[CH:9]=[CH:10][CH:11]=[C:2]2[NH:1][C:20](=[O:21])[CH3:19]

Komponenten

5

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 10112Calcium CarbonateHCID 657465-Amino-1-naphthol

Produkt 1

HCID 89653Acetamide, N-(5-hydroxy-1-naphthalenyl)-Ausbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5-amino-1-naphthol (17.6 g; 0.11 mol) in 500 ml of dioxane, there were added 11 g of calcium carbonate (0.11 mol) and, dropwise, 8 ml of chloroacetyl chloride (0.112 mol), with stirring and under an inert atmosphere. The reaction medium was heated at 80° C. for 2 hours 30 minutes. The suspension was cooled to room temperature, filtered on sintered glass and the inorganic salts were rinsed twice with dioxane. The mixture of the organic solutions was concentrated until an insoluble product appeared, and then poured over 400 ml of ice-cold water. The precipitate formed was drained, washed once with water and once with pentane. The brown powder obtained was dried under vacuum to a constant weight to give 16.8 g of N-(5-hydroxynaphthalen-1-yl)acetamide with a yield of 76%.

Aufarbeitung

  1. temperatureThe suspension was cooled to room temperature
  2. filtrationfiltered on sintered glass
  3. washthe inorganic salts were rinsed twice with dioxane
  4. additionThe mixture of the organic solutions
  5. concentrationwas concentrated until an insoluble product
  6. additionpoured over 400 ml of ice-cold water
  7. customThe precipitate formed
  8. washwashed once with water and once with pentane
  9. customThe brown powder obtained
  10. customwas dried under vacuum to a constant weight

Quellen und Nachweise

ORD-Eintrag
ord-55fcf9a0869941169b9bf0431bf74234
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605124B1

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