Sodium Iodide → HCID 13711329, Verbindung

HRID 620765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 620765
[O:1]=[C:2]([NH:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([OH:28])=[O:27])[C:3](=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])=[O:5].N([CH2:38][CH3:39])(CC)CC.[C:40](=[O:48])([O:44][CH:45](Cl)[CH3:46])[O:41][CH2:42][CH3:43].[Na+].[I-]>CC(C)=O>[CH2:42]([O:41][C:40]([O:44][CH:45]([O:27][C:26](=[O:28])[C:25]1[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=1[NH:23][C:2](=[O:1])[C:3](=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([O:11][CH:42]([O:41][C:40]([O:48][CH2:38][CH3:39])=[O:44])[CH3:43])=[O:10])=[O:5])[CH3:46])=[O:48])[CH3:43]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 162095Carbonic acid, 1-chloroethyl ethyl esterHCID 3062455Benzoic acid, 2,2'-((1,3-dioxo-2-(phenylmethylene)-1,3-propanediyl)diimino)bis-

Produkt 1

HCID 13711329HCID 13711329, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

The compound 11 (2.0 g, 4.7 mmol) and dry N(C2H5)3 (1.13 g, 11.2 mmol) were stirred in dry acetone (60 ml) at room temperature for 30 minutes. The mixture was treated with ethyl 1-chloroethyl carbonate (1.70 g, 11.2 mmol) and NaI (1.67 g, 11.2 mmol) and heated under reflux for 23 hours. After completion of the reaction, the precipitate was removed, and the solvent was removed frcm the filtrate. The residue was extracted with benzene, washed with saturated aqueous solution of NaHCO3 and saturated solution of NaCl and dried over anhydrous Na2SO4 . The solvent was evaporated to give a colorless viscous product. The resultant product was dissolved in developing solvent and purified by silica gel column chromatography (developing solvent: benzene:ether=95:5) to give the desired compound as white solid (1.34 g, crude yield, 44%). The solid was dissolved in methanol at room temperature, treated with water, and cooled with a solution of dry ice in acetone. The precipitated solid was filtered by suction, followed immediately by drying under reduced pressure to give the desired compound as white crystal (970 mg, yield, 32%). m.p., 48°-51° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 23 hours
  3. customAfter completion of the reaction
  4. customthe precipitate was removed
  5. customthe solvent was removed frcm the filtrate
  6. extractionThe residue was extracted with benzene
  7. washwashed with saturated aqueous solution of NaHCO3 and saturated solution of NaCl
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe solvent was evaporated
  10. customto give a colorless viscous product
  11. custompurified by silica gel column chromatography (developing solvent: benzene:ether=95:5)

Quellen und Nachweise

ORD-Eintrag
ord-fabc859588b540258e06d627aa61af48
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04822791

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