Hydrochloric Acid → HCID 86584401, compound

HRID 1280222Notes

Reaction equation

HRID 1280222 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[C:20]([Cl:21])=[CH:19][C:18]([O:22][CH2:23][CH:24]=[C:25]([Cl:27])[Cl:26])=[CH:17][C:16]=2[Cl:28])=[N:8][CH:9]=1)(=O)[CH3:2].Cl.[CH2:30]([O:32][NH2:33])[CH3:31].Cl>N1C=CC=CC=1>[CH2:30]([O:32][N:33]=[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[C:20]([Cl:21])=[CH:19][C:18]([O:22][CH2:23][CH:24]=[C:25]([Cl:27])[Cl:26])=[CH:17][C:16]=2[Cl:28])=[N:8][CH:9]=1)[CH3:2])[CH3:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 76850O-ethylhydroxylamine hydrochlorideHCID 18429976HCID 18429976, compound

Product 1

HCID 86584401HCID 86584401, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.41 g of 5-acetyl-2-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)pyridine and 10 ml of pyridine was added 0.17 g of O-ethylhydroxylamine hydrochloride. After stirring at room temperature for 24 hours, the reaction mixture was poured into diluted hydrochloric acid, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated to give a crude product. This crude product was subjected to silica gel chromatography, which afforded 0.40 g (yield, 89%) of 5-(1-(N-ethoxyimino)ethyl)-2-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)pyridine, nD24.5 1.5701.

Workup

  1. extractionextracted twice with diethyl ether
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give a crude product

Sources & evidence

ORD record
ord-dc0c5b46afbd4545be788005d76fd52d
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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