62921-76-0 → HCID 69199032, compound

HRID 1391699Notes

Reaction equation

HRID 1391699 reaction equation
[Br-].C([N+:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:10][CH:9]=1)CCCCC.N1C=CC(O)=CC=1.COCCOCCOCCOCCOS(C1C=CC(C)=CC=1)(=O)=O>>[CH3:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][C:11]1[CH:12]=[CH:13][N:8]=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 1241569162921-76-0HCID 178444689HCID 178444689, compound

Product 1

HCID 69199032HCID 69199032, compound

Conditions

Temperature
100 °C

Procedure

Preparation of 1-hexyl-4-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-pyridinium bromide—Pyridin-4-ol (1.50 g, 15.77 mmol) and toluene-4-sulfonic acid 2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester (5.62 g, 19.71 mmol) were combined in a 50 mL round bottomed flask equipped with condenser, magnetic stir bar, and a positive flow of nitrogen. The solution was heated in a 100° C. oil bath for 24 hrs. The solution was then cooled and placed on a vacuum line at 1 mmHg and heated at 80° C. for 6 hrs to removed residual starting materials. The by-product was removed via washing with deionized water (3×15 mL) to afford 4-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-pyridine. The product may be subsequently purified employing column chromatography techniques at this point or may proceed directly to the addition of 1-bromohexane (3.90 g, 23.66 mmol) in 25 mL tetrahydrofuran. Stirring the resulting reaction mixture at 50° C. for 24 hrs resulted in the desired product, 1-hexyl-4-(2-{2-[2-(2-ethoxy]-ethoxy}-ethoxy)-pyridinium bromide in a 38% yield (2.70 g, 5.99 mmol).

Workup

  1. customwere combined in a 50 mL round bottomed flask
  2. customequipped with condenser, magnetic stir bar
  3. temperatureThe solution was then cooled
  4. temperatureheated at 80° C. for 6 hrs
  5. customto removed residual
  6. customThe by-product was removed
  7. washvia washing with deionized water (3×15 mL)

Sources & evidence

ORD record
ord-c440f2d509f24d43b015f764c4e3c043
Source dataset
uspto-grants-2008_03
Patent number
US07339015B2

Reaction notes

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