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

HRID 1753698

反应方程式

HRID 1753698 反应方程式
[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

参与物

8

反应物 4

HCID 176醋酸HCID 660872-氰基噻吩HCID 70213丁二酸二异丙酯HCID 5360545钠2 次

产物 1

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

试剂、催化剂与溶剂 3

HCID 24380三氯化铁催化剂HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂HCID 6405叔戊醇溶剂2 次

反应条件

温度
85 °C

实验过程

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%).

后处理

  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%)

来源与证据

ORD记录
ord-91c2c12475a44be8a7aa62493dace166
来源数据集
uspto-grants-2015_10
专利号
US09166167B2

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