P-Anisidine → HCID 10421590, compound

HRID 467062Notes

Reaction equation

HRID 467062 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.I[CH2:11][CH2:12][CH2:13][CH3:14]>>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([N:7]([CH2:9][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 10962Butyl iodide

Product 1

HCID 10421590HCID 10421590, compoundYield 91.7%

Procedure

4-Methoxyaniline (10.5 g) in iodobutane (50 g) was heated under reflux overnight. Excess iodobutane was distilled off and final traces were removed in vacuo. The residue in DMF (dimethyl formamide) (50 mL) was treated with DABCO (1,4-diazobicyclo[2.2.2]octane) (20 g) and the mixture heated under reflux for 2 hours. Most of the DMF was then evaporated and the residue taken up in ethyl acetate, washed well with water, and dried (Na2SO4). After evaporation of the solvent the above procedure was repeated with iodobutane (50 mL) (overnight) followed by treatment with DABCO (10 g). After work-up, the resulting oil was chromatographed on silica gel eluting with 10% ethyl acetate in hexane to give 4-methoxy-N,N-dibutylaniline (9.2 g).

Workup

  1. temperatureunder reflux overnight
  2. distillationExcess iodobutane was distilled off
  3. customfinal traces were removed in vacuo
  4. additionThe residue in DMF (dimethyl formamide) (50 mL) was treated with DABCO (1,4-diazobicyclo[2.2.2]octane) (20 g)
  5. temperaturethe mixture heated
  6. temperatureunder reflux for 2 hours
  7. customMost of the DMF was then evaporated
  8. washwashed well with water
  9. dry with materialdried (Na2SO4)
  10. customAfter evaporation of the solvent the above procedure
  11. customwas repeated with iodobutane (50 mL) (overnight)
  12. customAfter work-up, the resulting oil was chromatographed on silica gel eluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1b3ce6b704ee4eb4a6cfcb5b0ca78551
Source dataset
uspto-grants-1992_10
Patent number
US05158949

Reaction notes

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