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

HRID 2212255ノート

反応式

HRID 2212255 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b74540d223ee4290b49d0765c2188141
出典データセット
uspto-grants-2006_09
特許番号
US07101905B2

反応ノート

読み込み中…