3,4,5,6-Tetrahydrophthalic anhydride → N-{2-fluoro-4-chloro-5-(2-methylcyclopentyl)oxyphenyl}-3,4,5,6-tetrahydrophthalimide

HRID 21466

반응식

HRID 21466 반응식
[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[CH3:16])=[CH:5][C:3]=1[NH2:4].[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2[CH2:23][CH2:24][CH2:25][CH2:26][C:18]1=2>C(O)(=O)C>[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[CH3:16])=[CH:5][C:3]=1[N:4]1[C:20](=[O:21])[C:19]2[CH2:23][CH2:24][CH2:25][CH2:26][C:18]=2[C:17]1=[O:22]

참가 물질

4

반응물 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 152793932-Fluoro-4-chloro-5-(2-methylcyclopentyl)oxyaniline

생성물 1

HCID 15279394N-{2-fluoro-4-chloro-5-(2-methylcyclopentyl)oxyphenyl}-3,4,5,6-tetrahydrophthalimide수율 98%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

2-Fluoro-4-chloro-5-(2-methylcyclopentyl)oxyaniline (660 mg, 2.71 mmol), 3,4,5,6-tetrahydrophthalic anhydride (503 mg, 3.31 mmol) and acetic acid (10 ml) were charged into a 50 cc round-bottom flask, and heated for 5 hours while refluxing. After completion of the reaction, the reaction solution was cooled to room temperature, and poured into ice-water (100 ml). The mixture was extracted with ethyl acetate (30 ml×3), and the organic layers were combined, washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, the solvent was distilled off under reduced pressure, and the resulting pale brown oily substance was purified by silica gel column chromatography (development solvent: hexane/ethyl acetate=9/1) to obtain N-{2-fluoro-4-chloro-5-(2-methylcyclopentyl)oxyphenyl}-3,4,5,6-tetrahydrophthalimide (1.00 g, 2.65 mmol, 98% yield).

후처리

  1. temperatureheated for 5 hours
  2. temperaturewhile refluxing
  3. customAfter completion of the reaction
  4. extractionThe mixture was extracted with ethyl acetate (30 ml×3)
  5. washwashed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  7. customThe drying agent was separated by filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe resulting pale brown oily substance was purified by silica gel column chromatography (development solvent: hexane/ethyl acetate=9/1)

출처 및 근거

ORD 기록
ord-79d3e5883c8e429ca585b0f3496eaa4c
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424277

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