Aldoxime → 4-(5-Trifluoromethyl-2-pyridyloxy)phenoxy[propionyl]-alpha-diethylaminoacetaldoxime

HRID 1583704Notes

Reaction equation

HRID 1583704 reaction equation
[CH:1](=[N:3][OH:4])[CH3:2].ClNC(=O)[CH2:8][CH2:9][C:10](N)=[O:11].C(NCC)C.C([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])C.[F:26][C:27]([F:48])([F:47])[C:28]1[CH:29]=[CH:30][C:31]([O:34][C:35]2[CH:46]=[CH:45][C:38]([O:39]C(C)C(Cl)=O)=[CH:37][CH:36]=2)=[N:32][CH:33]=1>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[F:47][C:27]([F:26])([F:48])[C:28]1[CH:29]=[CH:30][C:31]([O:34][C:35]2[CH:46]=[CH:45][C:38]([O:39][C:2]([C:10](=[O:11])[CH2:9][CH3:8])([N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])[CH:1]=[N:3][OH:4])=[CH:37][CH:36]=2)=[N:32][CH:33]=1

Participants

8

Reactant 5

HCID 7863AldoximeHCID 8021DiethylamineHCID 8471TriethylamineHCID 130552202-(4-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoyl chlorideHCID 15238416N-chlorosuccinamide

Product 1

HCID 867405104-(5-Trifluoromethyl-2-pyridyloxy)phenoxy[propionyl]-alpha-diethylaminoacetaldoxime

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Acetaldoxime (0.59 g, 0.01 mole) and N-chlorosuccinamide (1.34 g, 0.01 mole) were charged into a round-bottom flask which contained 5 milliliters (ml) of dimethylformamide (DMF). After the exotherm had subsided, a solution of diethylamine (0.73 g, 0.01 mole) and triethylamine (1.01 g, 0.01 mole) in 1.4 ml of DMF was added. After stirring for 1 hour at room temperature, 2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionyl chloride was added and the reaction was allowed to proceed to completion. The reaction mixture was then partitioned between ether and 1N hydrochloric acid. The ether layer was then washed with 5% potassium carbonate and brine. After drying over magnesium sulfate, the ether layer was concentrated in vacuo to afford the crude product. Chromatography employing 50 g of silica gel and hexane-ethyl acetate (2:1) as the eluent afforded 0.85 g of pure product which was identified by conventional techniques.

Workup

  1. customThe reaction mixture was then partitioned between ether and 1N hydrochloric acid
  2. washThe ether layer was then washed with 5% potassium carbonate and brine
  3. dry with materialAfter drying over magnesium sulfate
  4. concentrationthe ether layer was concentrated in vacuo
  5. customto afford the crude product

Sources & evidence

ORD record
ord-a7eda1ddf3524a1aadf41c56a3cb52e0
Source dataset
uspto-grants-1985_11
Patent number
US04554014

Reaction notes

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