Acetic Acid → 1,4-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione

HRID 1753698

反応式

HRID 1753698 の反応式
[Na].[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]#[N:8].[C:9]([O:19]C(C)C)(=O)[CH2:10][CH2:11][C:12]([O:14]C(C)C)=O.[C:23](O)(=O)[CH3:24]>C(O)(CC)(C)C.CO.[Fe](Cl)(Cl)Cl>[O:14]=[C:12]1[C:11]2=[C:7]([C:3]3[S:2][CH:6]=[CH:5][CH:4]=3)[NH:8][C:9](=[O:19])[C:10]2=[C:7]([C:3]2[S:2][CH:6]=[CH:23][CH:24]=2)[NH:8]1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 660872-ThiophenecarbonitrileHCID 70213Diisopropyl succinateHCID 5360545Sodium2 回

生成物 1

HCID 1785175291,4-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione

試薬・触媒・溶媒 3

HCID 24380Iron chloride (FeCl3)触媒HCID 887Methanol溶媒HCID 64052-Methyl-2-butanol溶媒2 回

反応条件

温度
85 °C

実験手順

Fine pieces of sodium metal (6.90 g, 0.30 mol) were added to 100 mL t-amyl alcohol and a small amount of iron (iii) chloride (100 mg) was added. The mixture was stirred vigorously for 2 hr at 105° C. until sodium disappeared. The solution was cooled at 85° C. 2-Thiophenecarbonitrile (22.0 g, 0.2 mol) was added to the resultant solution. Then diisopropyl succinate (16.6 g, 0.08 mol) was dissolved in 10 mL of t-amyl alcohol and added drop wise over 1 hr at 85° C. Reaction was stirred at this temperature for 12 hrs. The reaction mixture was then cooled to 50° C., diluted with 100 mL of methanol, and then slowly neutralized with 30 ml of glacial acetic acid and refluxed briefly, and the reaction mixture was filtered. After the residue was washed several times with hot methanol and water, the resultant solid was dried in vacuum oven at 50° C. A dark red colored powder was obtained which was used further without purification (20 g, 83%).

後処理

  1. additionadded drop wise over 1 hr at 85° C
  2. customReaction
  3. temperatureThe reaction mixture was then cooled to 50° C.
  4. temperaturerefluxed briefly
  5. filtrationthe reaction mixture was filtered
  6. washAfter the residue was washed several times with hot methanol and water
  7. customthe resultant solid was dried in vacuum oven at 50° C
  8. customA dark red colored powder was obtained which
  9. customwas used further without purification (20 g, 83%)

出典と根拠

ORDレコード
ord-91c2c12475a44be8a7aa62493dace166
出典データセット
uspto-grants-2015_10
特許番号
US09166167B2

関連ノート

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