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

HRID 885656Notes

Reaction equation

HRID 885656 reaction equation
[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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

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 mixture was stirred at room temperature, and sodium cyanide (ground to a powder just prior to use) (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 (9.5 g, 0.075 mol, 98% purity) were added, 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. After cooling overnight, water (100 mL) was added to the reaction mixture, and stirring was continued for 1 h. 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 (17.0 g).

Workup

  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. temperatureAfter cooling overnight
  7. stirringstirring
  8. filtrationThe mixture was filtered
  9. customthe solid collected
  10. washwas washed with water (3×50 mL), mesitylene (50 g)
  11. customdried to a constant weight in a vacuum-oven at 55° C.

Sources & evidence

ORD record
ord-c243666c5a6c4bb8a25bbdbb3e0eb2f5
Source dataset
uspto-grants-2012_08
Patent number
US08242279B2

Reaction notes

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