Acetic Acid → N-acetyl-N-2-octyl-4-iodoaniline

HRID 21430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 21430
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:10])=[CH:4][CH:3]=1.[C:17](O)(=[O:19])[CH3:18].C(OC(=O)C)(=O)C>CCOCC>[C:17]([N:8]([CH:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:10])[C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)(=[O:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 9927521N-(4'-iodophenyl)-2-aminooctane

Produkt 1

HCID 9907537N-acetyl-N-2-octyl-4-iodoanilineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A flask containing N-(4'-iodophenyl)-2-amino octane (1.50 g, 4.5 mmol) was charged with acetic acid (15 ml) and acetic anhydride (15 ml). The reaction flask was immersed in an oil bath which was warmed to 70° C. over a period of 0.5 hr. After stirring for 19 hrs, the reaction was allowed to cool, diluted with ether (200 ml), washed with water (2×50 ml), saturated aqueous sodium bicarbonate (4×50 ml), water (2×50 ml) and brine (50 ml), dried (Na2SO4), filtered, and evaporated in vacuo. Flash column chromatography (silica, 1:4; EtOAc:hexanes) provided N-acetyl-N-2-octyl-4-iodoaniline (1.48 g, 70%) as a white solid. Mp 60°-62° C.

Aufarbeitung

  1. customThe reaction flask was immersed in an oil bath
  2. temperatureto cool
  3. washwashed with water (2×50 ml), saturated aqueous sodium bicarbonate (4×50 ml), water (2×50 ml) and brine (50 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-729ea807b9614b928be9ddb5af805e35
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424056

Notizen zur Reaktion

Wird geladen…