Dihexylamine → HCID 10542715, compound

HRID 2245197Notes

Reaction equation

HRID 2245197 reaction equation
[CH2:1]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[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>[CH2:8]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 8920Dihexylamine2×HCID 9590p-Fluoronitrobenzene

Product 1

HCID 10542715HCID 10542715, compoundYield 81.6%

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 di-n-hexylamine (14.1 grams, 0.3 moles), 1-fluoro-4-nitrobenzene (14.1 grams, 0.1 moles) and anhydrous methyl sulfoxide (40 ml). The contents of the flask were heated at 100° C. for 20 hours; cooled to room temperature; partitioned between diethyl ether (300 ml) and water (100 ml); filtered. The ether layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield a yellow oil containing excess dihexylamine. The yellow oil was purified by passing through a short column of silica gel and elating with hexane (300 ml) to yield 25.0 grams of product as a yellow oil. 1H NMR (CDCl3) δ 8.1(d, 2H), 6.5(d, 2H), 3.3 5(t, 4H), 1.6(pent, 4H), 1.2-1.4(m, 12H), 0.9(t, 6H).

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. filtrationfiltered
  6. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield a yellow oil
  10. customThe yellow oil was purified

Sources & evidence

ORD record
ord-89ce7392f8094e2b9da09895f86e77a4
Source dataset
uspto-grants-2010_03
Patent number
US07683017B2

Reaction notes

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