p-Fluoronitrobenzene → HCID 59215595, compound

HRID 2245196Notes

Reaction equation

HRID 2245196 reaction equation
[CH2:1]([C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1>CS(C)=O>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([NH:11][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 363824-Hexylaniline

Product 1

HCID 59215595HCID 59215595, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a flask equipped with a magnetic stirrer, reflux condenser, and a nitrogen inlet was added 4-n-hexylaniline (49.1 grams, 0.283 moles), 1-fluoro-4-nitrobenzene (13.3 grams. 0.094 moles) and anhydrous methyl sulfoxide (80 ml). The contents of the flask were heated at 100° C. for 4 days; cooled to room temperature; partitioned between diethyl ether (300 ml) and water (100 ml). The ether extract was washed with water (4×100 ml) followed by brine (3×50 ml). The ether extract was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield a brown liquid. The brown liquid was recrystalized from hexane (500 ml) to yield 15.0 grams of product as a yellow solid. 1H NMR (CDCl3) δ 8.1(d, 2H), 7.2(d, 2H), 7.15(d, 2H),6.9(d, 2H), 6.3(bs, 1H), 2.6(t, 2H), 1.6(pent, 2H), 1.2-1.4(m, 6H), 0.9(t, 3H).

Workup

  1. customTo a flask equipped with a magnetic stirrer
  2. temperaturereflux condenser, and a nitrogen inlet
  3. temperaturecooled to room temperature
  4. custompartitioned between diethyl ether (300 ml) and water (100 ml)
  5. extractionThe ether extract
  6. washwas washed with water (4×100 ml)
  7. extractionThe ether extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto yield a brown liquid
  12. customThe brown liquid was recrystalized from hexane (500 ml)

Sources & evidence

ORD record
ord-5be5fa6b135f4f129472ab16473b542b
Source dataset
uspto-grants-2010_03
Patent number
US07683017B2

Reaction notes

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