Water → HCID 178485491, compound

HRID 1902563Notes

Reaction equation

HRID 1902563 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:8])([O-:3])=[O:2].[CH3:18][NH:19]C=O.O>C1(C)C(C)=CC=CC=1>[CH3:18][N:19]=[C:7]([OH:8])[C:6]1[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=1)[C:10]([OH:9])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 31254N-MethylformamideHCID 13442309HCID 13442309, compound

Product 1

HCID 178485491HCID 178485491, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

238.11 g (1 mol) of 3,5-dinitrophthalic anhydride are dissolved under reflux in 1 liter of xylene. 62.02 g (1.05 mols) of N-methylformamide are added dropwise under reflux in the course of 30 minutes. After 18 hours under reflux, the water formed and the formic acid, together with some xylene (total 140 ml), are distilled off, the boiling point rising to 137° C. The solution is filtered hot. After slow cooling and concentration of the mother liquor, 209.42 g (83% of theory) of 3,5-dinitrophthalic acid N-methylimide are obtained; melting point: 174°-6° C.

Workup

  1. temperatureunder reflux in the course of 30 minutes
  2. temperatureAfter 18 hours under reflux
  3. distillationthe formic acid, together with some xylene (total 140 ml), are distilled off
  4. customrising to 137° C
  5. filtrationThe solution is filtered hot
  6. temperatureAfter slow cooling

Sources & evidence

ORD record
ord-19124d91c7a347a09865f1695a6cd65d
Source dataset
uspto-grants-1982_12
Patent number
US04363917

Reaction notes

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