1-Methylimidazole → 2-Amino-5-cyano-N,3-dimethylbenzamide

HRID 885650Notes

Reaction equation

HRID 885650 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9](Br)=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].CC1C2C(=CC=CC=2)C=CC=1.[C-]#N.[Na+].[CH3:28][N:29]1C=CN=C1>[Cu]I.O>[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([C:28]#[N:29])=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 13901-MethylimidazoleHCID 70021-MethylnaphthaleneHCID 8929Sodium CyanideHCID 442275752-amino-5-bromo-N,3-dimethylbenzamide

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 100-mL, three-necked flask equipped with a mechanical stirrer, thermometer and condenser was charged with 2-amino-5-bromo-N,3-dimethylbenzamide (prepared by the method of Reference Example 1) (5.0 g, 0.02 mol, 99.1% purity) and 1-methylnaphthalene (20 g) while maintaining a flow of nitrogen through a gas inlet line connected to the condenser. The reaction mixture was stirred at room temperature and sodium cyanide (ground to a powder just prior to use) (1.25 g, 0.024 mol, assuming 95% purity), copper(I) iodide (0.57 g, 0.003 mol, 98% purity) and 1-methyl-1H-imidazole (1.40 g, 0.017 mol, 99%) were added. The mixture was heated to between 160 and 165° C. for 6 h and then transferred to a 200-mL flask and allowed to cool overnight. Water (20 mL) was added dropwise to the reaction mixture over 5 minutes while stirring. After stirring for an additional 2 h, the reaction mixture was filtered and the collected solid was washed with water (3×10 mL) and xylenes (10 mL) and dried to a constant weight in a vacuum-oven at 80° C. to give the title compound as a light brown solid (3.85 g).

Workup

  1. customA 100-mL, three-necked flask equipped with a mechanical stirrer
  2. temperaturewhile maintaining a flow of nitrogen through a gas inlet line
  3. temperatureThe mixture was heated to between 160 and 165° C. for 6 h
  4. customtransferred to a 200-mL flask
  5. temperatureto cool overnight
  6. stirringwhile stirring
  7. stirringAfter stirring for an additional 2 h
  8. filtrationthe reaction mixture was filtered
  9. washthe collected solid was washed with water (3×10 mL) and xylenes (10 mL)
  10. customdried to a constant weight in a vacuum-oven at 80° C.

Sources & evidence

ORD record
ord-24f6169525064f14b85083ff1ba438fa
Source dataset
uspto-grants-2012_08
Patent number
US08242279B2

Reaction notes

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