Hydrochloric Acid → 3-Chloro-2-methylbenzonitrile

HRID 1389510

Reaktionsgleichung

Reaktionsgleichung von HRID 1389510
[C-:1]#[N:2].[Na+].Cl.[Cl:5][C:6]1[C:7]([CH3:13])=[C:8]([CH:10]=[CH:11][CH:12]=1)N.N([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.C1(C)C=CC=CC=1>[Cl:5][C:6]1[C:7]([CH3:13])=[C:8]([CH:10]=[CH:11][CH:12]=1)[C:1]#[N:2]

Komponenten

8

Edukt 5

HCID 313Hydrochloric Acid2×HCID 68943-Chloro-2-methylanilineHCID 8929Sodium CyanideHCID 10340Sodium CarbonateHCID 23668193Sodium Nitrite

Produkt 1

HCID 5215083-Chloro-2-methylbenzonitrileAusbeute 52,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium cyanide (58 g, 1.18 mol) in 90 ml of water is added to cuprous chloride (44 g, 0.44 mol) in 180 ml of water while stirring mechanically in a 5 l. 3-necked flask. Evolution of heat results and the cuprous chloride dissolves. This is then cooled in an ice bath to 0° C. A milky suspension of cuprous cyanide results. To this is added 90 ml of toluene. 6 N Hydrochloric acid (125 ml) is added slowly to 3-chloro-2-methylaniline (50 g, 0.35 mol) in a 2 l. erlenmeyer flask, while cooling and swirling. A solution of sodium nitrite (25 g, 0.36 mol) in 70 ml of water is added dropwise to the hydrochloride suspension. Ice is added when required, keeping the temperature at 0° C. Anhydrous sodium carbonate is added until the diazonium hydrochloride solution is neutral to pH paper. This is then added slowly to the cold stirring cuprous cyanide suspension, the temperature not being allowed to rise above 5° C. The reaction is then stirred at 0°-5° C. for 0.5 hr, allowed to reach room temperature over a 2 hr period and then heated to 50° C. on the steam bath. After remaining at room temperature overnight, the product is steam distilled off. The distillate is extracted with benzene, washed with 10% hydrochloric acid, dried and evaporated to afford 28 g of the title compound that solidified on standing.

Aufarbeitung

  1. temperatureEvolution of heat
  2. customresults
  3. customresults
  4. temperatureerlenmeyer flask, while cooling
  5. additionIce is added when
  6. customat 0° C
  7. additionThis is then added slowly to the
  8. customto rise above 5° C
  9. stirringThe reaction is then stirred at 0°-5° C. for 0.5 hr
  10. temperatureheated to 50° C. on the steam bath
  11. waitAfter remaining at room temperature overnight
  12. distillationdistilled off
  13. extractionThe distillate is extracted with benzene
  14. washwashed with 10% hydrochloric acid
  15. customdried
  16. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f7c8e8662b8d49d6a03703ea1fab96e2
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04244966

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