2,2':5',2''-Terthiophene → (2,2':5',2''-Terthiophenyl)-5-carbonitrile

HRID 1646693

Reaktionsgleichung

Reaktionsgleichung von HRID 1646693
[CH:1]1[CH:2]=[C:3]([C:6]2[S:10][C:9]([C:11]3[S:15][CH:14]=[CH:13][CH:12]=3)=[CH:8][CH:7]=2)[S:4][CH:5]=1.ClS([N:20]=[C:21]=O)(=O)=O>C(Cl)Cl>[C:21]([C:14]1[S:15][C:11]([C:9]2[S:10][C:6]([C:3]3[S:4][CH:5]=[CH:1][CH:2]=3)=[CH:7][CH:8]=2)=[CH:12][CH:13]=1)#[N:20]

Komponenten

4

Edukt 2

HCID 650672,2':5',2''-TerthiopheneHCID 70918Chlorosulfonyl isocyanate

Produkt 1

HCID 184181(2,2':5',2''-Terthiophenyl)-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of α-terthienyl (2.46 g, 0.010 m) in methylene chloride (20 ml), was added chlorosulfonyl isocyanate (1.75 ml) in methylene chloride (15 ml). A yellow solid separated almost at once. The reaction mixture was stirred for 2 h and left overnight. Dimethyl formamide (5.0 ml) was added to the ice-cold reaction mixture dropwise. Addition of water (40 ml) precipitated a yellow solid insoluble in methylene chloride. The latter was removed in vacuo and the yellowish green solid was collected in a Buchner funnel and washed with water. Yield: 2 g; m.p. 122°-125° C. Recrystallization from the minimum amount of boiling ethanol-benzene(1:1) afforded 1.6 g of product(58.6% crude yield).

Aufarbeitung

  1. customA yellow solid separated almost at once
  2. waitleft overnight
  3. additionDimethyl formamide (5.0 ml) was added to the ice-cold reaction mixture dropwise
  4. additionAddition of water (40 ml)
  5. customprecipitated a yellow solid insoluble in methylene chloride
  6. customThe latter was removed in vacuo
  7. customthe yellowish green solid was collected in a Buchner funnel
  8. washwashed with water
  9. customRecrystallization from the minimum amount of boiling ethanol-benzene(1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8334b2bdb4be4dd98b1a850816167cdb
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05180838

Verknüpfte Notizen

Wird geladen…