Sodium docusate → (E)-1-(2-(3,7-dimethylocta-2,6-dienyloxy)-2-oxoethyl)-3-methyl-1H-imidazol-3-ium docusate

HRID 922002Notes

Reaction equation

HRID 922002 reaction equation
[Cl-].[CH3:2]/[C:3](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:4]\[CH2:5][O:6][C:7](=[O:15])[CH2:8][N:9]1[CH:13]=[CH:12][N+:11]([CH3:14])=[CH:10]1.[Na].[CH3:23][CH2:24][CH2:25][CH2:26][CH:27]([CH2:30][O:31][C:32]([CH2:34][CH:35]([S:47]([OH:50])(=[O:49])=[O:48])[C:36]([O:38][CH2:39][CH:40]([CH2:43][CH2:44][CH2:45][CH3:46])[CH2:41][CH3:42])=[O:37])=[O:33])[CH2:28][CH3:29]>CC(C)=O.O.O>[CH3:2]/[C:3](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:4]\[CH2:5][O:6][C:7](=[O:15])[CH2:8][N:9]1[CH:13]=[CH:12][N+:11]([CH3:14])=[CH:10]1.[CH3:23][CH2:24][CH2:25][CH2:26][CH:27]([CH2:30][O:31][C:32]([CH2:34][CH:35]([S:47]([OH:50])(=[O:49])=[O:48])[C:36]([O:38][CH2:39][CH:40]([CH2:43][CH2:44][CH2:45][CH3:46])[CH2:41][CH3:42])=[O:37])=[O:33])[CH2:28][CH3:29]

Participants

5

Reactant 2

HCID 9955175Sodium docusateHCID 86662343(E)-1-(2-(3,7-dimethylocta-2,6-dienyloxy)-2-oxoethyl)-3-methyl-1H-imidazol-3-ium chloride

Product 1

HCID 86662344(E)-1-(2-(3,7-dimethylocta-2,6-dienyloxy)-2-oxoethyl)-3-methyl-1H-imidazol-3-ium docusate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Imidazolium chloride [3] (312.8 mg, 1 mmol) and sodium docusate (444.6 mg, 1 mmol) were dissolved in 20 ml of acetone/H2O 1:1 and stirred overnight at room temperature. The remaining suspension was diluted with 50 ml of H2O and extracted with dichloromethane. The organic layer was washed successively with water until no more chloride ions could be detected in the washings (checked by addition of AgNO3 solution), dried over MgSO4 and the solvent was evaporated. Remaining volatile material was removed under reduced pressure (0.01 mbar) to give imidazolium docusate [4] in quantitative yield as yellow oil. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=9.07 (s, 1H), 7.71 (s, 2H), 5.33 (t, J=7.3 Hz, 1H), 5.24 (s, 2H), 5.07 (m, 1H), 4.69 (d, J=7.3 Hz, 2H), 3.91 (s, 3H), 3.90 (m, 4H), 3.62 (dd, J1=11.39 Hz, J2=3.88 Hz, 1H), 2.86 (m, 2H), 2.04 (m, 4H), 1.68 (s, 3H), 1.65 (s, 3H), 1.57 (s, 3H), 1.49 (m, 2H), 1.24 (m, 16 H), 0.84 (m, 12H). 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=171.1, 168.1, 166.9, 142.7, 137.7, 131.2, 123.7, 123.6, 123.4, 117.6, 66.2, 66.1, 62.4, 61.4, 49.5, 38.1, 356.0, 34.1, 29.8, 29.6, 28.3, 25.8, 25.5, 23.2, 23.0, 22.4, 17.6, 16.2, 13.9, 10.8. T5%onset 170° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed successively with water until no more chloride ions
  3. additioncould be detected in the washings (checked by addition of AgNO3 solution)
  4. dry with materialdried over MgSO4
  5. customthe solvent was evaporated
  6. customwas removed under reduced pressure (0.01 mbar)

Sources & evidence

ORD record
ord-aabe74ff181944e0bf32ea01ccdbfd55
Source dataset
uspto-grants-2016_03
Patent number
US09278134B2

Reaction notes

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