Iodine → N,N-Dibutyl-4-iodoaniline

HRID 2369630Notes

Reaction equation

HRID 2369630 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
12.5 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c6d12a6d9a644dae81d6e5212c9b15f3
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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