1-Bromopropane → N-(2-ethylhexyl)-N-propylaniline

HRID 361273

Reaktionsgleichung

Reaktionsgleichung von HRID 361273
[CH2:1]([CH:3]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:2].Br[CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([CH:3]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:4][N:5]([CH2:17][CH2:18][CH3:19])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 78401-Bromopropane2×HCID 11430Potassium CarbonateHCID 61484N-(2-Ethylhexyl)aniline

Produkt 1

HCID 53707404N-(2-ethylhexyl)-N-propylanilineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of N-(2-ethylhexyl)aniline (8.9 parts), 1-bromopropane (7.4 parts), anhydrous potassium carbonate (11 parts) and N,N-dimethylformamide (30 parts) was stirred at 125° C. for 24 hours. An additional quantity of 1-bromopropane (5 parts) was added and the mixture stirred for a further 18 hours at 125° C. The cooled mixture was filtered and poured into water. The product was extracted into dichloromethane and evaporated to yield N-(2-ethylhexyl)-N-propylaniline (8.9 parts, 78%) which was reacted with acetic anhydride prior to use to remove any unreacted starting materials.

Aufarbeitung

  1. stirringthe mixture stirred for a further 18 hours at 125° C
  2. filtrationThe cooled mixture was filtered
  3. additionpoured into water
  4. extractionThe product was extracted into dichloromethane
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-434cfdf0d3e64336a131d649a6b41c25
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05865857

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