반응 #555889

반응 방정식

acetic acid

2-thiophenecarbonitrile

sodium

Diisopropyl succinate

Sodium

→

2,5-dihydro-1,4-dioxo-3,6-dithienylpyrrolo[3,4-c]-pyrrole

용매

methanol

t-amyl alcohol

t-amyl alcohol

반응 조건

후처리

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   workup.ADDITIONwas added dropwise to the reaction mixture over 1 hr at 85° C
3. 3
   온도cooled to 50° C.
4. 4
   온도refluxed briefly
5. 5
   여과filtered
6. 6
   세척The residue was washed several times with hot methanol and water
7. 7
   기타the resultant solid was dried in a vacuum oven at 50° C
8. 8
   기타A dark red color powder was obtained which
9. 9
   기타was used without further purification (20 g, 83%)

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%).

출처