Water → 4-Methyl-3,5-dinitrobenzonitrile

HRID 968777Notes

Reaction equation

HRID 968777 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](O)=O)=[CH:9][C:8]=1[N+:19]([O-:21])=[O:20].S(N)([NH2:25])(=O)=O.O>S1(CCCC1)(=O)=O>[CH3:6][C:7]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:10]([C:11]#[N:25])=[CH:9][C:8]=1[N+:19]([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 82267SulfamideHCID 854773,5-Dinitro-p-toluic acid

Product 1

HCID 51343164-Methyl-3,5-dinitrobenzonitrileYield 91.2%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
120 °C

Procedure

Phosphorus oxychloride (27.2 kg) is added over 30 minutes to a mixture of 4-methyl-3,5-dinitrobenzoic acid (3) (20.7 kg) and sulfamide (19.9 kg) in sulfolane (118 kg). The mixture is heated to about 120° C. and aged for about 8 hours. After cooling to ambient temperature, water (104 L) is added and the mixture is cooled to about 5° C. to crystallize the product. After aging at least 1.5 hours, the product is isolated via centrifugation, and washed with water (142 L). The product is then removed from the centrifuge and dried in a convection tray dryer at about 60° C. until drying is complete to provide 4-methyl-3,5-dinitrobenzonitrile (4) (17.3 kg, 91% yield) as a tan solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. temperaturethe mixture is cooled to about 5° C.
  3. customto crystallize the product
  4. waitAfter aging at least 1.5 hours
  5. customthe product is isolated via centrifugation
  6. washwashed with water (142 L)
  7. customThe product is then removed from the centrifuge
  8. customdried in a convection tray dryer at about 60° C.
  9. customuntil drying

Sources & evidence

ORD record
ord-8a0bd33a12c54be5b961dd9f61867601
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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