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

HRID 468707

반응식

HRID 468707 반응식
[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

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 660872-ThiophenecarbonitrileHCID 70213Diisopropyl succinateHCID 5360545Sodium2회

생성물 1

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

시약·촉매·용매 3

HCID 24380Iron chloride (FeCl3)촉매HCID 887Methanol용매HCID 64052-Methyl-2-butanol용매2회

반응 조건

온도
85 °C

실험 절차

Sodium metal (6.90 g, 0.30 mol) was 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 the sodium dissolved. The solution was cooled to 85° C. and 2-thiophenecarbonitrile (22.0 g, 0.2 mol) was added. Diisopropyl succinate (16.6 g, 0.08 mol) dissolved in 10 ml of t-amyl alcohol was added dropwise to the reaction mixture over 1 hr at 85° C. The reaction mixture was stirred at this temperature for 12 hrs, 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 then filtered. The residue was washed several times with hot methanol and water, and the resultant solid was dried in a vacuum oven at 50° C. A dark red color powder was obtained which was used without further purification (20 g, 83%).

후처리

  1. dissolutiondissolved
  2. additionwas added dropwise to the reaction mixture over 1 hr at 85° C
  3. temperaturecooled to 50° C.
  4. temperaturerefluxed briefly
  5. filtrationfiltered
  6. washThe residue was washed several times with hot methanol and water
  7. customthe resultant solid was dried in a vacuum oven at 50° C
  8. customA dark red color powder was obtained which
  9. customwas used without further purification (20 g, 83%)

출처 및 근거

ORD 기록
ord-9346b47952254f16ac1197b02b0ba919
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08624232B2

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