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

HRID 922002
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HRID 922002 반응식
[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]
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 18366337Propan-2-one--water (1/1)
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-aabe74ff181944e0bf32ea01ccdbfd55
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09278134B2

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