1,1-Dichloroethane → 3,5-Dinitroaniline

HRID 1886154Notes

Reaction equation

HRID 1886154 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)C(O)=O)([O-:3])=[O:2].ClC(Cl)C.[N-:20]=[N+]=[N-].[Na+]>OS(O)(=O)=O.O=S(=O)=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[NH2:20])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 74333,5-Dinitrobenzoic acidHCID 33557Sodium Azide

Product 1

HCID 120683,5-DinitroanilineYield 87.9%

Reagents, catalysts & solvents 1

HCID 24681Fuming sulfuric acidSolvent

Procedure

3,5-Dinitrobenzoic acid (7, Aldrich) (106.1 grams, 0.50 mole) was dissolved in 400 milliliters of 23 to 24% oleum. Dichloroethane (480 milliliters) was added to this solution. Sodium azide (37 grams, 0.57 mole) was added in portions with stirring while maintaining the temperature below 25° C. The mixture was heated under reflux for 4 hours and allowed to cool to room temperature. The dichloroethane was removed by decantation, and the remaining mixture was poured over 9 liters of ice mixed with water. The yellow solid which separated was filtered, washed with water, and air dried to afford 80.5 grams (87.9%) of 8 with a melting point of 158° to 162° C.; literature: melting point of 162° to 163° C. (Reference 10). IR (KBr) 3335 (d, NHz), 3035, 1615 (C=O), 1575, 1525, 1440, 1325, 1090, 1050, 990, 915, 880, 810 and 730 cm -1.

Workup

  1. temperaturewhile maintaining the temperature below 25° C
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 4 hours
  4. customThe dichloroethane was removed by decantation
  5. additionthe remaining mixture was poured over 9 liters of ice
  6. additionmixed with water
  7. customThe yellow solid which separated
  8. filtrationwas filtered
  9. washwashed with water, and air
  10. customdried

Sources & evidence

ORD record
ord-dd867d91f2ed461288333a15817d1a9d
Source dataset
uspto-grants-1992_09
Patent number
US05149818

Reaction notes

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