Aniline → N,N-dihexadecylaniline

HRID 329353Notizen

Reaktionsgleichung

N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C([N:28]([CH:31]([CH3:33])[CH3:32])[CH2:29][CH3:30])(C)C>C1(C)C=CC=CC=1>[CH2:9]([N:28]([CH2:29][CH2:30][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:2])[C:31]1[CH:32]=[CH:11][CH:10]=[CH:9][CH:33]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Aniline (0.93 g), 1-iodohexadecane (10.56 g) and diisopropylethylamine (2.58 g) were combined in 10 ml of toluene. The mixture was heated at about 100° C. for a period of three days. The mixture was chromatographed on a silica gel column using 1% ethyl acetate in hexane. The heavy crystalline mass that precipitated from solution was cooled, diluted with ether and filtered. The filtrate was concentrated to an oil and applied to a silica gel column. The oil was washed with 500 ml of hexane followed by 1% ethyl acetate in hexane. The dialkylated fractions were combined and evaporated to give 2.6 grams of product.

Aufarbeitung

customThe mixture was chromatographed on a silica gel column
customThe heavy crystalline mass that precipitated from solution
temperaturewas cooled
additiondiluted with ether
filtrationfiltered
concentrationThe filtrate was concentrated to an oil
washThe oil was washed with 500 ml of hexane
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-e85b1ee711064a0684646b2befec4d4a
Quelldatensatz: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04891324

Notizen zur Reaktion

Wird geladen…