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

HRID 468707

Reaction equation

[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

Participants

Conditions

Temperature: 85 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-9346b47952254f16ac1197b02b0ba919
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08624232B2

Linked notes

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