Pyridine → 2-[(2-Chlorophenyl)methyl]-4-ethyl-4-methylisoxazolidine-3,5-dione

HRID 1155467Notes

Reaction equation

HRID 1155467 reaction equation
[CH2:1]([C:3]([CH3:10])([C:7](Cl)=[O:8])[C:4](Cl)=[O:5])[CH3:2].[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][NH:19][OH:20].N1C=CC=CC=1>C(Cl)Cl>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][N:19]1[C:4](=[O:5])[C:3]([CH2:1][CH3:2])([CH3:10])[C:7](=[O:8])[O:20]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 12811039Ethylmethylmalonyl chlorideHCID 12811040N-(2-ChlorobenZyl)hydroxylamine

Product 1

HCID 128110532-[(2-Chlorophenyl)methyl]-4-ethyl-4-methylisoxazolidine-3,5-dioneYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared in the manner of Example IV, using 8.2 grams (0.045 mole) of 2-ethyl-2-methylmalonyl dichloride, 7.1 grams (0.045 mole) of N-(2-chlorophenylmethyl)hydroxylamine and 16 ml of pyridine in 184 ml of methylene chloride. After purification on a silica gel column, 8.2 grams of 2-[(2-chlorophenyl)methyl]-4-ethyl-4-methylisoxazolidine-3,5-dione were obtained as an oil. The nmr and the ir spectra were consistent with the assigned structure.

Workup

  1. customThis compound was prepared in the manner of Example IV
  2. customAfter purification on a silica gel column

Sources & evidence

ORD record
ord-4164ce385cd242419c0412261e82f16c
Source dataset
uspto-grants-1981_11
Patent number
US04302238

Reaction notes

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