Water → 4-Methyl-3,5-dinitrobenzonitrile

HRID 968782Notes

Reaction equation

HRID 968782 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:10]([C:11]([NH2:13])=O)=[CH:9][C:8]=1[N+:19]([O-:21])=[O:20].O>C(#N)C>[CH3:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:10]([C:11]#[N:13])=[CH:9][C:8]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 33186984-Methyl-3,5-dinitrobenzamide

Product 1

HCID 51343164-Methyl-3,5-dinitrobenzonitrileYield 96.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Phosphorus oxychloride (91.3 kg) is added over about 30 minutes into a mixture of 4-methyl-3,5-dinitrobenzamide (6) (66.6 kg) in acetonitrile (250.2 kg). The mixture is heated at reflux (about 80° C.) for about 2.5 hours. The solution is then cooled to ambient temperature and added to water (335 L) over about 1.5 hour, while maintaining a temperature of less than about 30° C. The mixture is cooled to about 5° C. and held at this temperature for about 18 hours. The product that precipitates is isolated via centrifugation, washed with water (469 L), and dried in a convection tray dryer at about 45° C. for about 22 hours to provide 4-methyl-3,5-dinitrobenzonitrile (4) (59 kg, 96% yield).

Workup

  1. temperatureThe mixture is heated
  2. temperatureThe solution is then cooled to ambient temperature
  3. temperaturewhile maintaining a temperature of less than about 30° C
  4. temperatureThe mixture is cooled to about 5° C.
  5. customThe product that precipitates
  6. customis isolated via centrifugation
  7. washwashed with water (469 L)
  8. customdried in a convection tray dryer at about 45° C. for about 22 hours

Sources & evidence

ORD record
ord-88c3c7df44394f1282f2284913e5af4d
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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