Dimethylformamide → 3,4-Thiophenediacetonitrile, 2,5-dimethyl-

HRID 900981

Reaktionsgleichung

Reaktionsgleichung von HRID 900981
[C-:1]#[N:2].[K+].Cl[CH2:5][C:6]1[C:10]([CH2:11]Cl)=[C:9]([CH3:13])[S:8][C:7]=1[CH3:14].C[N:16]([CH:18]=O)C>C(Cl)(Cl)Cl.[Na+].[Cl-]>[C:1]([CH2:5][C:6]1[C:10]([CH2:11][C:18]#[N:16])=[C:9]([CH3:13])[S:8][C:7]=1[CH3:14])#[N:2]

Komponenten

6

Edukt 3

HCID 6228Dimethylformamide2×HCID 9032Potassium CyanideHCID 2883993,4-Bis(chloromethyl)-2,5-dimethylthiophene

Produkt 1

HCID 8190183,4-Thiophenediacetonitrile, 2,5-dimethyl-Ausbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5234Sodium ChlorideLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of potassium cyanide (13.2 g, 203 mmol) in DMF (66 mL) is cooled to 0° C. and carefully treated with a solution of 3,4-bis-chloromethyl-2,5-dimethyl-thiophene (10.0 g, 48.0 mmol) in DMF (34 mL). After warming to room temperature and stirring for 18 h, the solution is heated to 40° C. for 1 h, cooled to room temperature and diluted with chloroform and saturated aq NaCl. The chloroform layer is separated, and the aq layer extracted with chloroform. The combined organic layers are washed with saturated aq NaCl, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue is triturated with heptane, filtered under vacuum and dried overnight in a vacuum oven to give (4-cyanomethyl-2,5-dimethyl-thiophen-3-yl)-acetonitrile (8.6 g, 94.6%) as an off-white solid: mp 123.5-125.5° C.; Rf 0.33 (30% ethyl acetate in heptane); 1H NMR (CDCl3, 300 MHz) δ 3.65 (s, 4 H), 2.38 (s, 6 H).

Aufarbeitung

  1. temperatureAfter warming to room temperature
  2. temperaturethe solution is heated to 40° C. for 1 h
  3. temperaturecooled to room temperature
  4. customThe chloroform layer is separated
  5. extractionthe aq layer extracted with chloroform
  6. washThe combined organic layers are washed with saturated aq NaCl
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue is triturated with heptane
  11. filtrationfiltered under vacuum
  12. customdried overnight in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-633078a22eba4766b2697327ca066b54
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361671B2

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