Sodium Azide → 3-Methyl-2,5-dinitroaniline

HRID 544756Notes

Reaction equation

HRID 544756 reaction equation
[N+:1]([C:4]1[C:12]([CH3:13])=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:5]=1C(O)=O)([O-:3])=[O:2].[N-:17]=[N+]=[N-].[Na+]>OS(O)(=O)=O.O=S(=O)=O>[NH2:17][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[C:12]([CH3:13])[CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1

Participants

4

Reactant 2

HCID 33557Sodium Azide2×HCID 124953493-Methyl-2,5-dinitrobenzoic acid

Product 1

HCID 124953503-Methyl-2,5-dinitroanilineYield 95.4%

Reagents, catalysts & solvents 1

HCID 24681Fuming sulfuric acidSolvent

Procedure

2.43 grams of 2,5-dinitro-3-methylbenzoic acid was dissolved in 21.5 grams of oleum (20% SO3, 80% H2SO4). While the solution is stirred with the temperature maintained at 5°-10° C., 0.84 grams of powdered sodium azide was added cautiously in portions of less than 0.1 g over one hour. Rapid addition of the sodium azide was avoided to prevent any explosion from occurring. Stirring was continued for one hour at 0°-10° C. (gas evolution occurs), 10°-30° C. for two hours and 30°-60° C. for three hours. The resulting dark mixture was then poured over 200 ml of crushed ice to yield a yellow-orange precipitate. The mixture was filtered, washed with water and dried to give 2.02 g of 3-amino-2,5-dinitrotoluene (m.p. 125°-127° C.). Recrystallization from 95% ethanol gave rust colored flakes.

Workup

  1. temperaturemaintained at 5°-10° C.
  2. stirringStirring
  3. wait(gas evolution occurs), 10°-30° C. for two hours
  4. wait30°-60° C. for three hours
  5. customto yield a yellow-orange precipitate
  6. filtrationThe mixture was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-8936a942c5af44d4ad95bee00c06a1b5
Source dataset
uspto-grants-1984_05
Patent number
US04451681

Reaction notes

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