Water → 4-Methyl-3,5-dinitrobenzamide

HRID 968781Notes

Reaction equation

HRID 968781 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].S(N)([NH2:20])(=O)=O.O>N1C=CC=CC=1>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([NH2:20])=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

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

Product 1

HCID 33186984-Methyl-3,5-dinitrobenzamideYield 91.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
117.5 °C

Procedure

A mixture of 4-methyl-3,5-dinitrobenzoic acid (48.2 kg) (3) and sulfamide (50.1 kg) in pyridine (197 kg) is heated to reflux (about 115-120° C.) for about 1.5 hours. The solution is then cooled to ambient temperature and water is added (178 kg) over about 1 hour. The mixture is then cooled to about ˜5° C. and held at this temperature for about 1 hour. The product slurry is centrifuged and the solids obtained are washed with water (621 L). The product is dried in a vacuum tray dryer at a temperature of about 65° C. and a vacuum of about 10 torr to provide 4-methyl-3,5-dinitrobenzamide (6) (43.8 kg, 91.3% yield).

Workup

  1. temperatureis heated
  2. temperatureThe solution is then cooled to ambient temperature
  3. temperatureThe mixture is then cooled to about ˜5° C.
  4. customthe solids obtained
  5. washare washed with water (621 L)
  6. customThe product is dried in a vacuum tray dryer at a temperature of about 65° C.

Sources & evidence

ORD record
ord-9d0c720379864d6fb9a912a7d6b2ece3
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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