Methanol → n,n'-bis(4-hydroxyphenyl)benzene-1,4-dicarboxamide

HRID 258334Notes

Reaction equation

HRID 258334 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6]C=[CH:4][C:3]=1O.[C:9](Cl)(=[O:19])[C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1.[C:21]([O-:24])(O)=O.[Na+].[CH3:26][OH:27]>O.CC(C)=O>[OH:27][C:26]1[CH:6]=[CH:7][C:2]([NH:1][C:9](=[O:19])[C:10]2[CH:18]=[CH:17][C:13]([C:14]([NH:1][C:2]3[CH:3]=[CH:4][C:21]([OH:24])=[CH:6][CH:7]=3)=[O:15])=[CH:12][CH:11]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 887Methanol2×HCID 58012-Aminophenol2×HCID 7488Terephthaloyl chloride3×HCID 516892Sodium Bicarbonate2×

Product 1

HCID 244301n,n'-bis(4-hydroxyphenyl)benzene-1,4-dicarboxamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
56 °C

Procedure

N,N'-bis(4-hydroxyphenyl)terephthalamide (Structure V) was synthesized by the reaction of aminophenol with terephthaloyl chloride in the presence of NaHCO3. Two moles of aminophenol (218.3 grams) and 2 moles of NaHCO3 (168 grams) were first added to a stirred, round bottom flask containing 750 milliliters of acetone and 750 milliliters of deionized water. Two moles of terephthaloyl chloride (203.0 grams) were then added over a two hour period. During the course of the terephthaloyl chloride addition, 200 additional milliliters of acetone were also added to wash down the frothy suspension caused by CO2 evolution. After the terephthaloyl chloride addition, the precipitate produced from the reaction was collected by vacuum filtration. For purification of the precipitate obtained, one half of this material was placed in a stirred, round bottom flask containing 900 milliliters of methanol and 450 milliliters of deionized water. This suspension was heated to 56° C. and then vacuum filtered. For the solids recovered from this filtration, the washing step with methanol and deionized water was repeated. The filtrant solids obtained from the second hot filtration were then added to a stirred, round bottom flask containing 1250 milliliters of methanol. This suspension was vacuum filtered after 30 minutes to recover the solids for drying. After following the preceding washing procedure for the second half of the reaction precipitate, the total solids recovered were dried at 80° C. under vacuum for 5 hours. The weight of the dried solids was 325.6 grams, 93.4 percent of the theoretical yield to N,N'-bis(4-hydroxyphenyl)terephthalamide. The melting point of this final product was 405° C. as determined by DSC. ##STR13##

Workup

  1. additionwere also added
  2. washto wash down the frothy suspension
  3. additionAfter the terephthaloyl chloride addition
  4. customthe precipitate produced from the reaction
  5. filtrationwas collected by vacuum filtration
  6. customFor purification of the precipitate
  7. customobtained
  8. filtrationvacuum filtered
  9. filtrationFor the solids recovered from this filtration
  10. customThe filtrant solids obtained from the second hot filtration
  11. additionwere then added to a stirred, round bottom flask
  12. filtrationfiltered after 30 minutes
  13. customto recover the solids
  14. customfor drying
  15. washpreceding washing procedure for the second half of the reaction precipitate
  16. customthe total solids recovered
  17. customwere dried at 80° C. under vacuum for 5 hours

Sources & evidence

ORD record
ord-554612f2dd5b4a479605533ce4527033
Source dataset
uspto-grants-1993_11
Patent number
US05266661

Reaction notes

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