1,1-Dichloroethane → HCID 54348717, compound

HRID 1387338

Reaction equation

HRID 1387338 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

HCID 54348717HCID 54348717, compoundYield 34.5%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Dichloroethane (5 ml), thionyl chloride (0.65 g, 5.5 mmol) and N,N-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-1-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.

Workup

  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

Sources & evidence

ORD record
ord-818edd6a6ca140e39c2de4bea2a9049e
Source dataset
uspto-grants-2001_07
Patent number
US06268312B1

Linked notes

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