Water → HCID 728460, compound

HRID 1647541Notes

Reaction equation

HRID 1647541 reaction equation
N[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH:14]=[O:15])[CH3:13].[OH2:16]>>[C:6]([C:5]1[CH:4]=[C:3]2[C:11](=[O:16])[N:12]([C:13]3[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=3)[C:14](=[O:15])[C:2]2=[CH:10][CH:9]=1)([OH:8])=[O:7]

Participants

4

Reactant 3

HCID 962WaterHCID 9784-Aminobenzoic AcidHCID 6228Dimethylformamide

Product 1

HCID 728460HCID 728460, compoundYield 75%

Conditions

Temperature
140 °C

Procedure

38.42 g of trimellitic anhydride (0.2 moles), 27.4 g of p-amino-benzoic acid (0.2 moles) and 300 cc of N,N'-dimethylformamide are fed into a glass flask of 500 cc volume fitted with a mechanical stirrer, a thermometer and a vertical condenser. The reaction mixture is heated to 140° C. and left under stirring for three hours. On termination of this reaction time, the mixture is cooled to ambient temperature and poured into 2 liters of water under stirring. The precipitate is filtered off and washed repeatedly with methanol. After drying the product at 100° C. in a vacuum oven, 46.5 g of the product of the title are obtained. Yield 75%. The product structure is confirmed by NMR spectroscopy on a sample dissolved in deuterated dimethylsulphoxide.

Workup

  1. customfitted with a mechanical stirrer
  2. waitleft
  3. temperatureOn termination of this reaction time, the mixture is cooled to ambient temperature
  4. stirringunder stirring
  5. filtrationThe precipitate is filtered off
  6. washwashed repeatedly with methanol
  7. dry with materialAfter drying the product at 100° C. in a vacuum oven, 46.5 g of the product of the title
  8. customare obtained

Sources & evidence

ORD record
ord-e434a637b43d4d2297185607ac950f7c
Source dataset
uspto-grants-1995_07
Patent number
US05432248

Reaction notes

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