Pyridine → tert-butyl N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]carbamate

HRID 56017노트

반응식

HRID 56017 반응식
[Cl:1][C:2]1[C:3]([C:9](=O)[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[NH2:21][OH:22].N1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[C:3]([C:9](=[N:21][OH:22])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 118071648tert-butyl N-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]carbamate

생성물 1

HCID 136987059tert-butyl N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]carbamate수율 90.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 10.6 g of tert-butyl N-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]carbamate and 4.8 g of hydroxylamine hydrochloride in 87 ml of ethanol, 6.1 g of pyridine was added, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, the resulting residue was mixed with 50 ml of water and extracted with ethyl acetate (100 ml×2), the resulting organic layers were combined, dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 5:95 to 40:60) as the eluent to obtain 10.1 g of the desired product as a pale yellow resinous substance.

후처리

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. additionthe resulting residue was mixed with 50 ml of water
  4. extractionextracted with ethyl acetate (100 ml×2)
  5. dry with materialdried over saturated aqueous sodium chloride
  6. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-5f73139fd422490894bd4118cfd1b64b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434684B2

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