Cetylpyridinium Chloride → N-Hexadecylpyridinium 4-Cyanobenzenesulfinate

HRID 15614Notes

Reaction equation

HRID 15614 reaction equation
[Cl-].[CH2:2]([N+:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[C:24]([C:26]1[CH:31]=[CH:30][C:29]([S:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)#[N:25].[Na+]>C(O)C>[C:24]([C:26]1[CH:27]=[CH:28][C:29]([S:32]([O-:34])=[O:33])=[CH:30][CH:31]=1)#[N:25].[CH2:2]([N+:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 31239Cetylpyridinium ChlorideHCID 23668300Sodium 4-cyanobenzenesulfinate

Product 1

HCID 22055066N-Hexadecylpyridinium 4-CyanobenzenesulfinateYield 108.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of N-hexadecylpyridinium chloride (1.6 g) in ethanol (20 mL) was added to an Erlenmeyer flask containing a magnetically stirred boiling solution of sodium 4-cyanobenzenesulfinate (1.0 g) in anhydrous ethanol (200 mL). The mixture was allowed to cool to room temperature and was then further cooled in an ice bath. The mixture was filtered and the filtrate was concentrated to dryness using a rotary evaporator. The residue was then dissolved in chloroform (100 mL), filtered, and concentrated to dryness using a rotary evaporator to afford 2.4 g of product.

Workup

  1. additioncontaining
  2. temperaturewas then further cooled in an ice bath
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated to dryness
  5. customa rotary evaporator
  6. dissolutionThe residue was then dissolved in chloroform (100 mL)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customa rotary evaporator

Sources & evidence

ORD record
ord-f0da4c5f987e4c8bbde8d540ddba5cfb
Source dataset
uspto-grants-2010_06
Patent number
US07732633B2

Reaction notes

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