Triethylamine → 2-((2-Chlorophenyl)methyl)-4,4-dimethyl-1,2-oxazolidine-3,5-dione

HRID 1155462노트

반응식

HRID 1155462 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][OH:10].C(N(CC)CC)C.[CH3:18][C:19]([CH3:26])([C:23](Cl)=[O:24])[C:20](Cl)=[O:21]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:20](=[O:21])[C:19]([CH3:26])([CH3:18])[C:23](=[O:24])[O:10]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 4523180Dimethylmalonyl DichlorideHCID 12811040N-(2-ChlorobenZyl)hydroxylamine

생성물 1

HCID 128110462-((2-Chlorophenyl)methyl)-4,4-dimethyl-1,2-oxazolidine-3,5-dione수율 29.8%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

To a stirred solution of 8.3 grams (0.053 mole) of N-(2-chlorophenylmethyl)hydroxylamine and 12.1 grams (0.12 mole) of triethylamine in 200 ml of dry toluene was added dropwise a solution of 9.0 grams (0.053 mole) of dimethylmalonyl chloride in 50 ml of dry toluene. The addition required approximately 30 minutes and caused a white precipitate to form. The reaction mixture was stirred at room temperature for about 16 hours. The white precipitate was collected by filtration and washed with toluene. The combined wash and filtrate was washed with two portions of water and one portion of an aqueous solution saturated with sodium chloride and then dried with sodium sulfate. The solution was filtered from the sodium sulfate, and the filtrate was concentrated under reduced pressure to a viscous liquid. The liquid was subjected to column chromatography on silica gel. Elution was accomplished with 15% ethyl acetate in hexane. The fractions showing product by thin layer chromatography were combined to give an oil, which was distilled under reduced pressure to give 4.0 grams of 2-[(2-chlorophenyl)methyl]-4,4-dimethylisoxazolidine-3,5-dione; bp 115° C./0.03 mm. The nmr and the ir spectra were consistent with the assigned structure.

후처리

  1. additionThe addition required approximately 30 minutes
  2. customto form
  3. filtrationThe white precipitate was collected by filtration
  4. washwashed with toluene
  5. washThe combined wash
  6. washfiltrate was washed with two portions of water and one portion of an aqueous solution saturated with sodium chloride
  7. dry with materialdried with sodium sulfate
  8. filtrationThe solution was filtered from the sodium sulfate
  9. concentrationthe filtrate was concentrated under reduced pressure to a viscous liquid
  10. washElution
  11. customto give an oil, which
  12. distillationwas distilled under reduced pressure

출처 및 근거

ORD 기록
ord-23662a6ffb944885b11e5ec0f2fc422a
출처 데이터셋
uspto-grants-1981_11
특허 번호
US04302238

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