4-(4-Chlorophenoxy)aniline → 1-[4-(4-Chloro-phenoxy)-phenyl]-pyrrolidine-2,5-dione

HRID 1972186노트

반응식

HRID 1972186 반응식
[C:1]1(=[O:7])[O:6][C:4](=O)[CH2:3][CH2:2]1.[CH:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:9]=1.O=S(Cl)Cl>C1(C)C=CC=CC=1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:10]2[CH:11]=[CH:12][C:13]([N:14]3[C:1](=[O:7])[CH2:2][CH2:3][C:4]3=[O:6])=[CH:8][CH:9]=2)=[CH:17][CH:18]=1

참가 물질

5

반응물 3

HCID 75784-(4-Chlorophenoxy)anilineHCID 7922Succinic anhydrideHCID 24386Thionyl Chloride

생성물 1

HCID 218348381-[4-(4-Chloro-phenoxy)-phenyl]-pyrrolidine-2,5-dione수율 83%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

A mixture of succinic anhydride (250 mg, 2.50 mmol) and 4-amino-4′-chloro diphenylether (500 mg, 2.27 mml) in toluene is heated to 110° C. for 14 h. and cooled down to room temperature. SOCl2 (1.5 mL) is added into the mixture and stirred at room temperature for 8 h. After the solvent is removed under vacuum, the residue is treated with saturated NaHCO3 aqueous solution (20 mL) and extracted with CHCl3 (3×50 mL). The combined organic layer is washed with brine and dried (MgSO4). After filtering the drying agent, the filtrate is concentrated and purified by flash column chromatography (silica gel, EtOAc/hexane 30%˜80%) to provide 1-[4-(4-chloro-phenoxy)-phenyl]-pyrrolidine-2,5-dione as white solid (570 mg, 83%).

후처리

  1. temperaturecooled down to room temperature
  2. customAfter the solvent is removed under vacuum
  3. additionthe residue is treated with saturated NaHCO3 aqueous solution (20 mL)
  4. extractionextracted with CHCl3 (3×50 mL)
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationAfter filtering the drying agent
  8. concentrationthe filtrate is concentrated
  9. custompurified by flash column chromatography (silica gel, EtOAc/hexane 30%˜80%)

출처 및 근거

ORD 기록
ord-27372413f40c435287ff7bf4b98e13d5
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431607B2

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