Water → HCID 54552025, compound

HRID 1196994Notes

Reaction equation

HRID 1196994 reaction equation
[CH3:1][N:2]([CH3:43])[CH2:3][CH2:4][CH:5]=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([CH2:21][CH2:22][O:23]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:20][C:7]1=2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[CH3:43][N:2]([CH3:1])[CH2:3][CH2:4][CH:5]=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([CH2:21][CH2:22][OH:23])=[CH:20][C:7]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 54078769HCID 54078769, compound

Product 1

HCID 54552025HCID 54552025, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In this example, 0.92 g of 11-(3-dimethylaminopropylidene)-2-(2-triphenylmethyloxyethyl)-6,11-dihydrodibenz[b,e]oxepin is dissolved in a mixed solvent of 20 ml of water and 20 ml of dioxane. To the solution is added 60 mg of p-toluene sulfonic acid and the mixture is heated at reflux for two hours. The solvent is distilled away under reduced pressure and the residue is extracted with 200 ml of ethylacetate, washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium hydrochloride solution in oder and dried over anhydrous sodium sulfate. The solvent is distilled away under reduced pressure. The resultant residue is purified by column chromatography on silica gel (eluent: ethylacetate triethylamine=10:1 ) to obtain 0.4 g of the desired product.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for two hours
  3. distillationThe solvent is distilled away under reduced pressure
  4. extractionthe residue is extracted with 200 ml of ethylacetate
  5. washwashed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium hydrochloride solution in oder
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent is distilled away under reduced pressure
  8. customThe resultant residue is purified by column chromatography on silica gel (eluent: ethylacetate triethylamine=10:1 )

Sources & evidence

ORD record
ord-d8124520e49c47729b4394b0ca3ac6ef
Source dataset
uspto-grants-1992_05
Patent number
US05116863

Reaction notes

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