Toluene → (Pyridin-2-yl)(thiophen-2-yl)acetonitrile

HRID 1679770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1679770
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]#[N:8].Cl[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C1(C)C=CC=CC=1.[NH2-].[Na+]>O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[C:7]#[N:8]

Komponenten

6

Edukt 4

HCID 1140Toluene2×HCID 79772-ChloropyridineHCID 24533Sodium amideHCID 728802-Thienylacetonitrile

Produkt 1

HCID 14337913(Pyridin-2-yl)(thiophen-2-yl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a well-stirred solution containing 61.5 g. of 2-thienylacetonitrile and 56.5 g. of 2-chloropyridine in 400 ml. of toluene, slowly add a stirred suspension of 40 g. of sodamide in 300 ml. of toluene keeping the reaction temperature at 60°-65° C by cooling with an ice bath. After completing the addition maintain the temperature at 60° C for 2 hrs., add 200 ml. of water to the cooled reaction mixture, decant the tarry by-products and separate the aqueous layer. Evaporate in vacuo the resulting solution and dilute the thick black residue with 300 ml. of ether. Filter the separated solid and evaporate the filtrate. The desired product is distilled off at 145°-150° C/1 ml. and is recrystallized from alcohol to yield α-(2-thienyl)-2-pyridylacetonitrile, m.p. 48°-50° C.

Aufarbeitung

  1. additionTo a well-stirred solution containing 61.5 g
  2. additiona stirred suspension of 40 g
  3. additionthe addition
  4. addition, add 200 ml
  5. customdecant the tarry by-products
  6. customseparate the aqueous layer
  7. customEvaporate in vacuo the resulting solution
  8. additiondilute the thick black residue with 300 ml
  9. filtrationFilter the separated solid
  10. customevaporate the filtrate
  11. distillationThe desired product is distilled off at 145°-150° C/1 ml
  12. customand is recrystallized from alcohol

Quellen und Nachweise

ORD-Eintrag
ord-a47b637acb114e378a2f5e40e5097bfd
Quelldatensatz
uspto-grants-1978_03
Patentnummer
US04081544

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