Potassium Iodide → N-(2-phthalimido)ethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline

HRID 482052노트

반응식

HRID 482052 반응식
[F:1][C:2]([F:15])([CH:12]([F:14])[F:13])[CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1.Br[CH2:17][CH2:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29].C(=O)(O)[O-].[K+].[I-].[K+]>CN(C)C=O>[C:20]1(=[O:29])[N:19]([CH2:18][CH2:17][NH:9][C:8]2[CH:10]=[CH:11][C:5]([O:4][CH2:3][C:2]([F:15])([F:1])[CH:12]([F:13])[F:14])=[CH:6][CH:7]=2)[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]12

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 516893Potassium BicarbonateHCID 187663254-(2,2,3,3-Tetrafluoropropoxy)aniline

생성물 1

HCID 19065098N-(2-phthalimido)ethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline수율 41.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-(2,2,3,3-tetrafluoropropoxy)aniline (7.4 g), N-(2-bromoethyl)phthalimide (9.0 g), potassium bicarbonate (6.9 g), potassium iodide (5.5 g) and N,N-dimethylformamide (80 ml) are refluxed for 22 hours. The solvent was distilled off under reduced pressure. To the residue, ice-water (200 ml) and ethyl acetate (200 ml) were added and fractionated. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluate; ethyl acetate:hexane=1:2 v/v) and recrystallized from ethyl acetate-diisopropyl ether to give N-(2-phthalimido)ethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline (5.4 g) as white crystals.

후처리

  1. temperatureare refluxed for 22 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionTo the residue, ice-water (200 ml) and ethyl acetate (200 ml) were added
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled off under reduced pressure
  7. customThe residue was purified by silica gel chromatography (eluate; ethyl acetate:hexane=1:2 v/v)
  8. customrecrystallized from ethyl acetate-diisopropyl ether

출처 및 근거

ORD 기록
ord-5ef2bfb864914e8ea758dd7d32bb027b
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792780

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