Water → Maleic acid anilide

HRID 1682162Notes

Reaction equation

HRID 1682162 reaction equation
O.[C:2]1(=[O:8])[O:7][C:5](=[O:6])[CH:4]=[CH:3]1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C(C)=CC=CC=1.CN(C)C=O>[C:10]1([NH:9][C:2](=[O:8])/[CH:3]=[CH:4]\[C:5]([OH:7])=[O:6])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 7923Maleic Anhydride2×

Product 1

HCID 1550938Maleic acid anilide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 7237O-XyleneSolvent3×

Conditions

Temperature
80 °C

Procedure

To a 300 ml flask equipped with a water separator, reflux condenser, stirrer and a thermometer, 15.44 g of maleic anhydride (hereinafter abbreviated as MAN), 70 ml of xylene (hereinafter abbreviated as Xy) and 10 ml of dimethylformamide (hereinafter abbreviated as DMF) were charged. A mixture of 13.97 g of aniline (hereinafter abbreviated as AN) and 20 ml of xylene was added with stirring at 80° C. at a constant rate over 15 minutes and further aged for 15 minutes to obtain N-phenylmaleamic acid as a white slurry. To the slurry, 2.04 g (2.5% by mole per mole of MAN) of zinc N-phenylmaleamate/dimethylformamide adduct (hereinafter abbreviated as Zn(PMA)2.DMF) was added and the mixture was heated to reflux with stirring. Water generated by the reaction was removed by azeotropic distillation and the reaction was carried out at about 140° C. for 3.5 hours. The white slurry of PMA gradually dissolved as the dehydration reaction progressed and an orange yellow solution was obtained from which the catalyst component precipitated.

Workup

  1. temperaturereflux condenser, stirrer
  2. additionwere charged
  3. additionwas added
  4. waitfurther aged for 15 minutes

Sources & evidence

ORD record
ord-e16bc75442d142f3b96ff5357e812c00
Source dataset
uspto-grants-1992_12
Patent number
US05175309

Reaction notes

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