M-Phenylenediamine → N,N'-(m-phenylene)bis citraconamic acid

HRID 1939405Notes

Reaction equation

HRID 1939405 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 22883495N,N'-(m-phenylene)bis citraconamic acidYield 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. The solution was stirred as 112 g (1.0 mole) of citraconic anhydride in 500 ml of reagent acetone was added dropwise over about 11/2 hours 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. additionwas added dropwise over about 11/2 hours as the temperature
  4. temperatureThe reaction mixture was refluxed for an additional hour
  5. filtrationsuction filtered

Sources & evidence

ORD record
ord-c7c2f81ee4d540daa0682f25fa519e6e
Source dataset
uspto-grants-1997_12
Patent number
US05696188

Reaction notes

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