Pyridine → HCID 54021124, compound

HRID 1004377Notes

Reaction equation

HRID 1004377 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:14][C:15]1[CH:35]=[CH:34][C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27](=[N:31][O:32][CH3:33])[C:28]([NH2:30])=O)=[CH:17][CH:16]=1.N1C=CC=CC=1>CCOCC>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27](=[N:31][O:32][CH3:33])[C:28]#[N:30])=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 86584673HCID 86584673, compound

Product 1

HCID 54021124HCID 54021124, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Trifluoroacetic anhydride (3.15 g, 15 mmol) was added to a mixture of 2-(4-chlorophenoxymethyl)-α-methoxyiminophenylacetamide (1.19 g, 6 mmol) and pyridine (12 ml) under ice-cooling over 20 minutes, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, ether (150 ml) was added, and the mixture was washed with 1N hydrochloric acid (150 ml), water (100 ml) and saturated aqueous sodium bicarbonate solution (100 ml). The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(4-chlorophenoxymethyl)-α-methoxyiminophenylacetonitrile (1.57 g, 87.0%) as colorless crystals.

Workup

  1. temperaturecooling over 20 minutes
  2. additionwas added
  3. washthe mixture was washed with 1N hydrochloric acid (150 ml), water (100 ml) and saturated aqueous sodium bicarbonate solution (100 ml)
  4. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-b864ae8c399849fdbace2c8e0ef43c49
Source dataset
uspto-grants-2000_04
Patent number
US06048885

Reaction notes

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