Sodium Chloride → 1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonic acid;2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide

HRID 2403128Notes

Reaction equation

HRID 2403128 reaction equation
[CH3:1][CH2:2][N:3]([CH2:6][C:7]([NH:9][C:10]1[C:11]([CH3:17])=[CH:12][CH:13]=[CH:14][C:15]=1[CH3:16])=[O:8])[CH2:4][CH3:5].Cl.[Na].[CH3:20][CH2:21][CH2:22][CH2:23][CH:24]([CH2:27][O:28][C:29]([CH2:31][CH:32]([S:44]([OH:47])(=[O:46])=[O:45])[C:33]([O:35][CH2:36][CH:37]([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:38][CH3:39])=[O:34])=[O:30])[CH2:25][CH3:26].[Na+].[Cl-].C(Cl)(Cl)Cl>CO>[CH3:5][CH2:4][N:3]([CH2:6][C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:17])=[O:8])[CH2:2][CH3:1].[CH3:20][CH2:21][CH2:22][CH2:23][CH:24]([CH2:27][O:28][C:29]([CH2:31][CH:32]([S:44]([OH:47])(=[O:46])=[O:45])[C:33]([O:35][CH2:36][CH:37]([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:38][CH3:39])=[O:34])=[O:30])[CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 5234Sodium Chloride2×HCID 6212Chloroform2×HCID 6314Lidocaine HydrochlorideHCID 9955175Sodium docusate

Product 1

HCID 177558781,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonic acid;2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Lidocaine hydrochloride (0.0188 mol) was dissolved in 50 mL methanol and sodium docusate [bis(2-ethylhexyl)sulfosuccinate sodium salt] (0.0188 mol) was dissolved in 50 mL. The two solutions were combined and stirred for two hours, during this time a white precipitate (NaCl) formed. The methanol was removed by rotary evaporation which leaves a white sticky solid. To this solid, 150 mL of chloroform was added. A portion of the product dissolved the chloroform while the byproduct (NaCl) remained as a suspended solid. The NaCl was removed by filtration, and the solvent was removed by rotary evaporation. The product, lidocaine docusate, is a colorless syrup and is dried under high vacuum. 1H and 13C NMR (CDCl3) were obtained.

Workup

  1. customformed
  2. customThe methanol was removed by rotary evaporation which
  3. customleaves a white sticky solid
  4. customThe NaCl was removed by filtration
  5. customthe solvent was removed by rotary evaporation
  6. customis dried under high vacuum
  7. custom1H and 13C NMR (CDCl3) were obtained

Sources & evidence

ORD record
ord-5ad1200d74a84540b3186fa14c6c892d
Source dataset
uspto-grants-2014_08
Patent number
US08802596B2

Reaction notes

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