Diethyl Ether → HCID 22221209, compound

HRID 1389004Notes

Reaction equation

HRID 1389004 reaction equation
Cl.NO.[CH2:4]([O:6][C:7](=[O:23])[C:8]([C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])=[CH:9][N:10](C)C)[CH3:5].C([O-])(=O)C.[Na+].CCOCC>CO>[CH2:4]([O:6][C:7]([C:8]1[CH:9]=[N:10][O:22][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])=[O:23])[CH3:5]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 54095551HCID 54095551, compound

Product 1

HCID 22221209HCID 22221209, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Hydroxylamine hydrochloride (1.1 g.; 0.016 mol.) was added to a mixture of ethyl-2-(2',4'-dichlorobenzoyl)-3-dimethylaminopropenoate (4.74 g.; 0.015 mol.) and anhydrous sodium acetate (1.25 g.; 0.015 mol.) in 50 ml. of ether and 25 ml. of methanol at 25° C. An additional 25 ml. of methanol was added, and the resultant mixture was stirred for 30 minutes. The mixture was washed into a separatory funnel with 150 ml. of ether and the ether layer was washed free of salts with water. The ether layer was dried with magnesium sulfate, filtered, then concentrated to yield an oil which was crystallized from pentane to yield ethyl-5-(2',4'-dichlorophenyl)-4-isoxazolecarboxylate (1.88 g.; 44% yield) as tan crystals having a melting point of 82°-84° C. and the following analysis:

Workup

  1. customat 25° C
  2. washThe mixture was washed into a separatory funnel with 150 ml
  3. washof ether and the ether layer was washed free of salts with water
  4. dry with materialThe ether layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield an oil which
  8. customwas crystallized from pentane

Sources & evidence

ORD record
ord-594bb2ab955649c890d8bf7406cdc853
Source dataset
uspto-grants-1981_01
Patent number
US04243406

Reaction notes

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