p-Toluidine → HCID 13442302, compound

HRID 851553Notes

Reaction equation

HRID 851553 reaction equation
[N+:1]([C:4]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1>C(O)(=O)C>[C:22]1([CH3:25])[CH:23]=[CH:24][C:19]([N:18]2[C:10](=[O:11])[C:5]3=[C:4]([N+:1]([O-:3])=[O:2])[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[C:6]3[C:7]2=[O:9])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 7813p-ToluidineHCID 13442309HCID 13442309, compound

Product 1

HCID 13442302HCID 13442302, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2 kg (8.4 mols) of 3,5-dinitrophthalic anhydride and 897 g (8.4 mols) of p-toluidine in 6.2 l of glacial acetic acid are kept under reflux for 3 hours. After cooling, the mixture is filtered, the residue is rinsed with 2 l of water and then suspended in 25 l of water, and the product is filtered off and dried at 100° C. in vacuo. 2,339 g (85% of theory) of N-(p-toluyl)-3,5-dinitrophthalimide are obtained; melting point: 182°-3° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. washthe residue is rinsed with 2 l of water
  5. filtrationthe product is filtered off
  6. customdried at 100° C. in vacuo

Sources & evidence

ORD record
ord-9045923016f347cc829951cac96a09ab
Source dataset
uspto-grants-1983_05
Patent number
US04385182

Reaction notes

Loading…