M-Phenylenediamine → HCID 22883495, compound

HRID 2256

Reaction equation

HRID 2256 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[C:9]1(=[O:16])[O:15][C:13](=[O:14])[CH:12]=[C:10]1[CH3:11]>CC(C)=O>[C:1]1([NH:8][C:13](=[O:14])/[CH:12]=[C:10](/[CH3:11])\[C:9]([OH:16])=[O:15])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:13](=[O:14])/[CH:12]=[C:10](/[CH3:11])\[C:9]([OH:15])=[O:16])[CH:2]=1

Participants

4

Reactant 2

HCID 7935M-PhenylenediamineHCID 12012Citraconic Anhydrides

Product 1

HCID 22883495HCID 22883495, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

A 3-liter, 3-neck round bottom flask was charged with 54 g (0.5 mole) of m-phenylenediamine and 500 ml of reagent acetone and flushed with nitrogen. The flask was fitted with a reflux condenser, mechanical stirrer and thermocouple. A dropping funnel containing 112 g (1.0 mole) of citraconic anhydride in 500 ml of reagent acetone was attached and the solution added dropwise over about 1 1/2 hours with stirring as the temperature was allowed to rise to reflux the acetone. The reaction mixture was refluxed for an additional hour, cooled to room temperature and suction filtered to give 166 g of N,N'-(m-phenylene)bis citraconamic acid as shown by NMR analysis, as a tan mustard-colored solid melting at 152°-156° C.

Workup

  1. customflushed with nitrogen
  2. customThe flask was fitted with a reflux condenser, mechanical stirrer
  3. additionthe solution added dropwise over about 1 1/2 hours
  4. temperatureThe reaction mixture was refluxed for an additional hour
  5. filtrationsuction filtered

Sources & evidence

ORD record
ord-81e816ae13fd471baa1f76ede4d59949
Source dataset
uspto-grants-1998_03
Patent number
US05728757

Linked notes

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