Mesitylene → 2-Amino-5-cyano-N,3-dimethylbenzamide

HRID 885657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885657
[OH-].[Na+].Cl[O-].[Na+].[NH2:6][C:7]1[C:16]([CH3:17])=[CH:15][C:14](Br)=[CH:13][C:8]=1[C:9]([NH:11][CH3:12])=[O:10].C1(C)C=C(C)C=C(C)C=1.[C-]#N.[Na+].[CH2:31]([N:35]1C=CN=C1)CCC>[Cu]I.O>[NH2:6][C:7]1[C:16]([CH3:17])=[CH:15][C:14]([C:31]#[N:35])=[CH:13][C:8]=1[C:9]([NH:11][CH3:12])=[O:10]

Komponenten

8

Edukt 5

HCID 7947MesityleneHCID 8929Sodium CyanideHCID 61347ButylimidazoleHCID 442275752-amino-5-bromo-N,3-dimethylbenzamideHCID 86647248NaOH NaClO

Produkt 1

HCID 251572822-Amino-5-cyano-N,3-dimethylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A 500-mL four-necked flask equipped with a mechanical stirrer, thermocouple, condenser, side-arm addition funnel and sodium hydroxide/sodium hypochlorite scrubber was charged with 2-amino-5-bromo-N,3-dimethylbenzamide (prepared by the method of Reference Example 1) (24.6 g, 0.10 mol, 99% purity) and mesitylene (100 g) while maintaining an atmosphere of nitrogen through a gas inlet line connected to the condenser. The reaction mixture was stirred at room temperature, and granular sodium cyanide (Alfa Aesar®, 7.7 g, 0.15 mol, assuming 95% purity), copper(I) iodide (2.9 g, 0.015 mol, 98% purity) and 1-butyl-1H-imidazole (10.8 g, 0.085 mol, 98% purity) were added to the reaction mixture, after which time the nitrogen inlet line was attached directly to the reaction flask. The reaction mixture was heated at reflux (about 166-170° C.) for 6 h, while venting through the scrubber and then allow to cool overnight. Water (100 mL) was added to the reaction mixture and stirring was continued for 45 minutes. More water (25 mL) was added to the reaction mixture and stirring continued for an additional 15 minutes. The mixture was filtered, and the solid collected was washed with water (3×50 mL), mesitylene (50 g) and dried to a constant weight in a vacuum-oven at 55° C. to give the title compound as a light yellow solid (16.8 g).

Aufarbeitung

  1. customA 500-mL four-necked flask equipped with a mechanical stirrer
  2. additionthermocouple, condenser, side-arm addition funnel
  3. temperaturewhile maintaining an atmosphere of nitrogen through a gas inlet line
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux (about 166-170° C.) for 6 h
  6. temperatureto cool overnight
  7. stirringstirring
  8. stirringstirring
  9. waitcontinued for an additional 15 minutes
  10. filtrationThe mixture was filtered
  11. customthe solid collected
  12. washwas washed with water (3×50 mL), mesitylene (50 g)
  13. customdried to a constant weight in a vacuum-oven at 55° C.

Quellen und Nachweise

ORD-Eintrag
ord-d5959d86d1fa4de9b1fe48d2c137aae7
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242279B2

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