Diethyl Ether → HCID 22221355, compound

HRID 1389011Notes

Reaction equation

HRID 1389011 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])=[C:16]([Cl:21])[CH:15]=1)=[CH:9][N:10](C)C)[CH3:5].C([O-])(=O)C.[Na+].C(OCC)C>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])=[C:16]([Cl:21])[CH:15]=1)=[O:23])[CH3:5]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 53723120HCID 53723120, compound

Product 1

HCID 22221355HCID 22221355, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxylamine hydrochloride (0.7 g.; 0.01 mol.) was added to a mixture of ethyl-2-(3',4'-dichlorobenzoyl)-3-di-methylaminopropenoate (3.16 g.; 0.01 mol.) and sodium acetate (0.82 g.; 0.01 mol.) in 25 ml. of diethyl ether and 15 ml. of methanol. The resultant mixture was stirred at 25° C. for 16 hours until the reaction was complete. The reaction mixture was filtered and concentrated in vacuo. The residue was dissolved in chloroform, extracted with water, dried over magnesium sulfate and concentrated in vacuo. Recrystallization with ethanol yielded ethyl-5-(3',4'-dichlorophenyl)-4-isoxazolecarboxylate as a white solid (1.5 g.; 52.4% yield) having a melting point of 108°-110° C. and the following analysis:

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. extractionextracted with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customRecrystallization with ethanol

Sources & evidence

ORD record
ord-fe198963ee314e3ca8d29862791ce0ae
Source dataset
uspto-grants-1981_01
Patent number
US04243406

Reaction notes

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