Chlorosuccinimide → Ethyl 2-chloro-2-[2-(4-methoxyphenyl)hydrazono]acetate

HRID 896803

반응식

HRID 896803 반응식
[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[N:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH3:2].[Cl:17]N1C(=O)CCC1=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:16])[C:5]([Cl:17])=[N:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH3:2]

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 69445862[(4-Methoxyphenyl)hydrazono]acetic acid ethyl ester

생성물 1

HCID 21829645Ethyl 2-chloro-2-[2-(4-methoxyphenyl)hydrazono]acetate수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
2.5 °C

실험 절차

Method A. A solution of [(4-methoxyphenyl)hydrazono]acetic acid ethyl ester (33, 4.0 g, 18.0 mmol) in anhydrous THF (40 mL) was treated with N-chlorosuccinimide (NCS, 2.52 g, 18.9 mmol, 1.05 equiv) at 0-5° C. under N2, and the resulting reaction mixture was stirred at 0-5° C. for an additional 30 min before being gradually warmed to 25° C. for 12 h. When HPLC and TLC showed the reaction was deemed complete, the solvent was removed in vacuo. The residue was directly purified by column chromatography (SiO2, 0-25% EtOAc/hexane gradient elution) to afford the desired chloro[(4-methoxyphenyl)hydrazono]acetic acid ethyl ester (34, 3.51 g, 4.62 g theoretical, 76%) as pale-yellow solids, which was found to be essentially pure to do the following reaction without further purification. For 34, CIMS m/z 255/257 (M+−H, C11H13ClN2O3).

후처리

  1. customthe resulting reaction mixture
  2. temperaturebefore being gradually warmed to 25° C. for 12 h
  3. customthe solvent was removed in vacuo
  4. customThe residue was directly purified by column chromatography (SiO2, 0-25% EtOAc/hexane gradient elution)

출처 및 근거

ORD 기록
ord-faaa910d7ff54efdb3b96a45e6efe9a5
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919451B2

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