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

HRID 554701Notes

Reaction equation

HRID 554701 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].CC1C=C(C)C=C(C)C=1.[C-]#N.[Na+].[CH3:26][NH:27]CCNC>[Cu]I.O>[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([C:26]#[N:27])=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 7947MesityleneHCID 8070N,N'-DimethylethylenediamineHCID 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 Example 1) (99.1% purity, 5.0 g, 0.02 mol) and 1,3,5-trimethylbenzene (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 powdered sodium cyanide (powdered just prior to use) (1.25 g, 0.024 mol, assuming 95% purity), copper(I) iodide (0.57g, 0.003 mol) and N,N′-dimethylethylenediamine (1.51 g, 0.017 mol) were added. The reaction mixture was heated to between about 138 and 140° C. for 3 h, then heated to reflux (about 155° C.), and then cooled to 23° C., and water (20 mL) was added over 5 minutes. The mixture was stirred for 30 minutes and then filtered. The solid collected was washed with water (2×10 mL), chlorobenzene (10 mL), and then dried to constant a weight in a vacuum-oven at 50° C. to give the title compound (3.3 g) as an off-white solid melting at 202-203° C.

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 reaction mixture was heated to between about 138 and 140° C. for 3 h
  4. temperatureheated
  5. temperatureto reflux (about 155° C.)
  6. temperaturecooled to 23° C.
  7. stirringThe mixture was stirred for 30 minutes
  8. filtrationfiltered
  9. customThe solid collected
  10. washwas washed with water (2×10 mL), chlorobenzene (10 mL)
  11. customdried to constant a weight in a vacuum-oven at 50° C.

Sources & evidence

ORD record
ord-93e053beeee44f1ab2d785a55d52e5bc
Source dataset
uspto-grants-2011_11
Patent number
US08049029B2

Reaction notes

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