Phthalic Anhydride → 2-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-4-phenyl-thiophene-3-carboxylic acid ethyl ester

HRID 2212255노트

반응식

HRID 2212255 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH2:17])=[O:5])[CH3:2].[C:18]1(=O)[O:23][C:21](=[O:22])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[N:17]1[C:21](=[O:22])[C:20]2[C:19](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]1=[O:23])=[O:5])[CH3:2]

참가 물질

4

반응물 2

HCID 6811Phthalic AnhydrideHCID 73242Ethyl 2-amino-4-phenylthiophene-3-carboxylate

생성물 1

HCID 70358872-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-4-phenyl-thiophene-3-carboxylic acid ethyl ester수율 70%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 2-amino-4-phenylthiophene-3-carboxylic acid ethyl ester (2 mmol, Example 1, Part B) and phthalic anhydride (2.2 mmol) in glacial acetic acid (20 mL) was heated at reflux overnight. After cooling to room temperature, the acetic acid was removed in vacuo and the residue triturated with petroleum ether. The crude product was collected by filtration, suspended in acetyl chloride (5 mL), and heated to reflux for one hour. After removing the solvent in vacuo, the residue was dissolved in ethyl acetate (30 mL), washed sequentially with 5% aqueous NaHCO3 (10 mL), water (10 mL), brine (10 mL), dried (Na2SO4), filtered, and concentrated in vacuo. Recrystallization from petroleum ether afforded the desired product as a yellow solid in 70% yield.

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customthe acetic acid was removed in vacuo
  4. customthe residue triturated with petroleum ether
  5. filtrationThe crude product was collected by filtration
  6. temperatureheated
  7. temperatureto reflux for one hour
  8. customAfter removing the solvent in vacuo
  9. dissolutionthe residue was dissolved in ethyl acetate (30 mL)
  10. washwashed sequentially with 5% aqueous NaHCO3 (10 mL), water (10 mL), brine (10 mL)
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customRecrystallization from petroleum ether

출처 및 근거

ORD 기록
ord-b74540d223ee4290b49d0765c2188141
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101905B2

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