Iodine → N,N-Dibutyl-4-iodoaniline

HRID 2369630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369630
[I:1]I.[CH2:3]([N:7]([CH2:14][CH2:15][CH2:16][CH3:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][CH2:5][CH3:6].C([O-])(O)=O.[Na+].CCOCC>O>[I:1][C:11]1[CH:12]=[CH:13][C:8]([N:7]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][CH2:4][CH2:5][CH3:6])=[CH:9][CH:10]=1

Komponenten

6

Edukt 4

HCID 807IodineHCID 3283Diethyl EtherHCID 61154N,N-DibutylanilineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 13169159N,N-Dibutyl-4-iodoanilineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
12.5 °C

Versuchsvorschrift

Iodine (7.88 g, 31 mmol) was added portionwise to a mixture of N,N-dibutylaniline (7 g, 34 mmol) and NaHCO3 (2.87 g, 34 mmol) in water (25 mL) with stirring at 10-15° C. After 1 h the mixture was poured into Et2O (200 mL), washed with water (100 mL), Na2S2O3 (2×100 mL), water (2×100 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed on silica using hexane as eluent. The first fraction was collected and the solvent removed under reduced pressure to give the title compound (7.26 g, 71%) as a pale brown oil.

Aufarbeitung

  1. washwashed with water (100 mL), Na2S2O3 (2×100 mL), water (2×100 mL)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customThe residue was chromatographed on silica
  5. customThe first fraction was collected
  6. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c6d12a6d9a644dae81d6e5212c9b15f3
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703978B2

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