6-Bromo-1-hexanol → N-ethyl-N-(6-hydroxyhexyl)-4-bromoaniline

HRID 1004776

Reaktionsgleichung

Reaktionsgleichung von HRID 1004776
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH3:2].C(N(CC)C(C)C)(C)C.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27]>O>[CH2:1]([N:3]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 779706-Bromo-1-hexanolHCID 81531DiisopropylethylamineHCID 117456564-bromo-N-ethylaniline

Produkt 1

HCID 18793525N-ethyl-N-(6-hydroxyhexyl)-4-bromoanilineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

36.8 g (184.1 mmols) of N-ethyl-4-bromoaniline, 48.1 ml (1.5-fold equivalent weight) of N,N-diisopropylethylamine and 28.9 ml (1.2 equivalent) of 6-bromohexanol were mixed, and the mixture obtained was heated at 110° C. for 14 hours in an atmosphere of argon. Water was added to the reaction solution obtained, which was then extracted with ethyl acetate. The organic layer obtained was dried with anhydrous magnesium sulfate and then concentrated. The residue thus obtained was heated under reduced pressure (160° C./0.3 torr), and the components distilled out were removed to obtain 55.6 g of crude N-ethyl-N-(6-hydroxyhexyl)-4-bromoaniline (yield: 100%; a dark-brown oily liquid).

Aufarbeitung

  1. customthe mixture obtained
  2. customobtained
  3. extractionwhich was then extracted with ethyl acetate
  4. customThe organic layer obtained
  5. dry with materialwas dried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue thus obtained
  8. temperaturewas heated under reduced pressure (160° C./0.3 torr)
  9. distillationthe components distilled out
  10. customwere removed

Quellen und Nachweise

ORD-Eintrag
ord-43f38d4b835a4852888afb02c2db9b16
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06051722

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