Water → 4-Methyl-3,5-dinitrobenzonitrile

HRID 968784Notes

Reaction equation

HRID 968784 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:7][C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:11]([C:12]([NH2:14])=O)=[CH:10][C:9]=1[N+:20]([O-:22])=[O:21].O.[OH-].[NH4+]>C(#N)C>[CH3:7][C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:11]([C:12]#[N:14])=[CH:10][C:9]=1[N+:20]([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 24819Phosphorus pentachlorideHCID 33186984-Methyl-3,5-dinitrobenzamide

Product 1

HCID 51343164-Methyl-3,5-dinitrobenzonitrileYield 75.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Phosphorus pentachloride (1.082 g) is added over about 30 minutes into a mixture of 4-methyl-3,5-dinitrobenzamide (6) (1.04 g) in acetonitrile (20 mL, 15 g). The mixture is then heated to about 60° C. for about 4 hours. The solution is then cooled to ambient temperature and is slowly added to an ice and water mixture (20 mL). The mixture is cooled to about 5° C., whereupon ammonium hydroxide is added until a pH of about 8 is attained. The product that precipitates is filtered, washed with water (10 mL), and dried to provide 4-methyl-3,5-dinitrobenzonitrile (4) (0.72 g, 75% Yield).

Workup

  1. temperatureThe solution is then cooled to ambient temperature
  2. additionis added until a pH of about 8
  3. customThe product that precipitates
  4. filtrationis filtered
  5. washwashed with water (10 mL)
  6. customdried

Sources & evidence

ORD record
ord-d593099b5264428aab91c65b49810e6b
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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