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

HRID 554700Notes

Reaction equation

HRID 554700 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].ClC1C=CC=CC=1.[C-]#N.[Na+].[CH3:24][NH:25]CCNC>[Cu]I.O>[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([C:24]#[N:25])=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 7964ChlorobenzeneHCID 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 chlorobenzene (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 (0.57 g, 0.003 mol) and N,N′-dimethylethylenediamine (1.51 g, 0.017 mol) were added. The mixture was heated at reflux (about 130° C.) for 4.5 h and then cooled to 25° C., and water (20 mL) was added over 5 minutes, and the resulting mixture was stirred for 30 minutes. The mixture was filtered, and the solid collected was washed with water (2×10 mL) and chlorobenzene (10 mL), and then dried to a constant weight in a vacuum-oven at 50° C. to give the title compound (3.6 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 mixture was heated
  4. temperatureat reflux (about 130° C.) for 4.5 h
  5. temperaturecooled to 25° C.
  6. stirringthe resulting mixture was stirred for 30 minutes
  7. filtrationThe mixture was filtered
  8. customthe solid collected
  9. washwas washed with water (2×10 mL) and chlorobenzene (10 mL)
  10. customdried to a constant weight in a vacuum-oven at 50° C.

Sources & evidence

ORD record
ord-cbd0763facfe487a8b50fa35d8e2be21
Source dataset
uspto-grants-2011_11
Patent number
US08049029B2

Reaction notes

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