2-Chlorobenzaldehyde → [2-(2-Thienyl)ethylamino](2-chlorophenyl)acetonitrile

HRID 568122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 568122
[C-:1]#[N:2].[Na+].Cl.[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][CH2:11][NH2:12].[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O>O.C(O)C>[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][CH2:11][NH:12][CH:16]([C:15]1[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=1[Cl:13])[C:1]#[N:2]

Komponenten

6

Edukt 3

HCID 69962-ChlorobenzaldehydeHCID 8929Sodium CyanideHCID 4585722-Thiopheneethylamine, hydrochloride

Produkt 1

HCID 10858772[2-(2-Thienyl)ethylamino](2-chlorophenyl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

9.8 g (0.2 mol) of sodium cyanide is dissolved in 70 ml of water and to the solution first 32.8 g (0.2 mol) of 2-(2-thienyl)ethylamine hydrochloride, then in a period of a few minutes, the solution of 28.2 g (0.2 mol) of o-chlorobenzaldehyde in 30 ml of ethanol are added. During the addition the temperature of the mixture raises to 45° C. The reaction mixture is then stirred at 60° C. for 2 hours, then cooled to room temperature and diluted with 50 ml of water. The resulting oily product is extracted with 100 ml of 1,2-dichloroethane, the organic phase is washed to cyanide-free with 2×50 ml of water, the traces of 2-(2-thienyl)ethylamine are removed by treatment with 20 ml of 3% hydrochloric acid solution. The residual fast crystallizing oil is the product. Weight: 52 g (94%) mp.: 40-41° C. The product was identified as written in Example 1. Quality of the product is identical with that of the product prepared according to Example 1.

Aufarbeitung

  1. waitin a period of a few minutes
  2. additionDuring the addition the temperature of the mixture
  3. temperaturecooled to room temperature
  4. extractionThe resulting oily product is extracted with 100 ml of 1,2-dichloroethane
  5. washthe organic phase is washed to cyanide-free with 2×50 ml of water
  6. customthe traces of 2-(2-thienyl)ethylamine are removed by treatment with 20 ml of 3% hydrochloric acid solution
  7. customThe residual fast crystallizing oil
  8. customprepared

Quellen und Nachweise

ORD-Eintrag
ord-02bb7fa70abb45699dd03f37b0c01ecf
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180793B2

Notizen zur Reaktion

Wird geladen…