1,1-Dichloroethane → HCID 54348717, Verbindung

HRID 279453

Reaktionsgleichung

Reaktionsgleichung von HRID 279453
ClC(Cl)C.S(Cl)(Cl)=O.[CH3:9][C:10]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[N:24][O:25][CH3:26])[C:21]([OH:23])=O.O[N:33]=[C:34]([NH2:37])[CH2:35][CH3:36]>CCOCC.N1C=CC=CC=1.CN(C)C=O>[CH3:26][O:25][N:24]=[C:20]([C:21]1[O:23][N:37]=[C:34]([CH2:35][CH3:36])[N:33]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][O:12][C:11]1[CH:27]=[C:28]([CH3:31])[CH:29]=[CH:30][C:10]=1[CH3:9]

Komponenten

8

Edukt 4

HCID 63651,1-DichloroethaneHCID 24386Thionyl ChlorideHCID 4092053N-HydroxypropionimidamideHCID 54397424HCID 54397424, Verbindung

Produkt 1

HCID 54348717HCID 54348717, VerbindungAusbeute 34,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Dichloroethane (5 ml), thionyl chloride (0.65 g, 5.5 mmol) and dimethylformamide (0.05 ml) were added to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetic acid (1.57 g, 5 mmol), and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the mixture was concentrated under reduced pressure, pyridine (3 ml) and 1-hydroxyimino-l-propylamine (0.88 g, 10 mmol) were added to the residue, and the mixture was stirred under reflux for 0.5 hours. After completion of the reaction, ether (150 ml) was added, and the mixture was washed with 1N hydrochloric acid (150 ml) twice. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl 3-ethyl-1,2,4-oxadiazol-5-yl ketone O-methyloxime (0.63 g, 34.5%) as colorless crystals.

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. customAfter completion of the reaction
  3. additionwere added to the residue
  4. stirringthe mixture was stirred
  5. temperatureunder reflux for 0.5 hours
  6. additionwas added
  7. washthe mixture was washed with 1N hydrochloric acid (150 ml) twice
  8. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customthe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  11. customrecrystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-250ef4a0f16e479a96bb861e252fb002
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362212B1

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