Phthalic Anhydride → 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(3-methoxyphenyl)-thiophene-3-carboxylic acid ethyl ester

HRID 270197ノート

反応式

HRID 270197 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[CH:9][S:8][C:7]=1[NH2:19])=[O:5])[CH3:2].[C:20]1(=O)[O:25][C:23](=[O:24])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]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]=[C:13]([O:17][CH3:18])[CH:12]=2)=[CH:9][S:8][C:7]=1[N:19]1[C:23](=[O:24])[C:22]2[C:21](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]1=[O:25])=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 6811Phthalic AnhydrideHCID 690667Ethyl 2-amino-4-(3-methoxyphenyl)thiophene-3-carboxylate

生成物 1

HCID 670738502-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-(3-methoxyphenyl)-thiophene-3-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 2-amino-4-(3-methoxyphenyl)-thiophene-3-carboxylic acid ethyl ester (2 mmol, Example 18 & 19, Part B) and phthalic anhydride (2.2 mmol) in glacial acetic acid (20 mL) is heated at reflux overnight. After cooling to room temperature, the acetic acid is removed in vacuo and the residue triturated with petroleum ether. The crude product is collected by filtration, suspended in acetyl chloride (5 mL), and heated to reflux for one hour. After removing the solvent in vacuo, the residue is 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 affords the desired product.

後処理

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. customthe acetic acid is removed in vacuo
  4. customthe residue triturated with petroleum ether
  5. filtrationThe crude product is collected by filtration
  6. temperatureheated
  7. temperatureto reflux for one hour
  8. customAfter removing the solvent in vacuo
  9. dissolutionthe residue is 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

出典と根拠

ORDレコード
ord-963058f091aa483e847ff638eb967971
出典データセット
uspto-grants-2008_11
特許番号
US07449490B2

反応ノート

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