Water → 2-Amino-4-methyl-3,5-dinitrobenzonitrile

HRID 968786Notes

Reaction equation

HRID 968786 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([CH3:14])[C:8]([N+:15]([O-:17])=[O:16])=[CH:7][C:3]=1[C:4]([NH2:6])=O.P(Cl)(Cl)(Cl)=O.O>C(#N)C>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([CH3:14])[C:8]([N+:15]([O-:17])=[O:16])=[CH:7][C:3]=1[C:4]#[N:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 590163082-Amino-4-methyl-3,5-dinitrobenzamide

Product 1

HCID 167267892-Amino-4-methyl-3,5-dinitrobenzonitrileYield 83.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 2-amino-4-methyl-3,5-dinitrobenzamide (7) (12.5 kg) in acetonitrile (78.4 kg) is added phosphorus oxychloride (14.8 kg) over a period of about 35 minutes. The mixture is then heated to reflux. After approximately 3.25 hours, the mixture is cooled to about 25° C. and added to water (245 kg). The vessel that formerly contained the reaction mixture is rinsed with acetonitrile (16 kg) and the rinse solution is also added to the aforementioned water quench solution. The quench solution is then cooled to about 5° C. over a period of about 2 hours. The quench solution is then filtered, the vessel that formerly contained the quench solution is rinsed with water (93 kg), and the rinse solution is passed through the product-containing filter. The product obtained is then dried in a vacuum tray drier, at a temperature of about 47° C. and a vacuum of about 12 torr, to provide 2-amino-4-methyl-3,5-dinitrobenzonitrile (5) (9.6 kg, 83.5% yield).

Workup

  1. temperatureThe mixture is then heated to reflux
  2. washis rinsed with acetonitrile (16 kg)
  3. additionthe rinse solution is also added to the aforementioned water
  4. customquench solution
  5. temperatureThe quench solution is then cooled to about 5° C. over a period of about 2 hours
  6. filtrationThe quench solution is then filtered
  7. washis rinsed with water (93 kg)
  8. filtrationfilter
  9. customThe product obtained
  10. customis then dried in a vacuum tray drier, at a temperature of about 47° C.

Sources & evidence

ORD record
ord-1de3cf504e4e48b0be389b4dfbf79621
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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