Hydrochloric Acid → N,N'-Diphenylterephthaldiamide

HRID 258331Notes

Reaction equation

HRID 258331 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8](Cl)(=[O:18])[C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.Cl.[OH-].[Na+]>CC(C)=O>[C:2]1([NH:1][C:8](=[O:18])[C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:14])=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6115Aniline3×HCID 7488Terephthaloyl chloride3×HCID 14798Sodium Hydroxide

Product 1

HCID 252156N,N'-DiphenylterephthaldiamideYield 84.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

N,N'-diphenylterephthalamide (Structure I) is synthesized from aniline and terephthaloyl chloride using acetone as a reaction media and an aqueous solution of NAOH to neutralize the HCl generated. Terephthaloyl chloride (87.2 grams, 0.43 moles) is first added to a stirred, 2-liter reaction flask containing one liter of acetone. After the terephthaloyl chloride has dissolved, aniline (80.0 grams, 0.86 moles) is added dropwise using an addition funnel over a 30 minute period. During the course of this addition, a white precipitate is formed. A 200 ml aqueous solution of NaOH (34.3 grams, 0.86 moles) is then added, also using an addition funnel, over a 30 minute period. The reaction temperature during both the aniline and NAOH addition is maintained below 35° C. by blowing air onto the outside of the reaction flask. After the NAOH addition, the reaction mixture is stirred for three hours and then vacuum filtered (filtrate pH=7). The filter cake obtained is washed with 400 ml of acetone and then added to one liter of deionized water, stirred for 15 minutes and filtered. This filter cake is washed with 500 ml of acetone and then dried in a 105° C. vacuum oven to a constant weight. This final product (114.4 grams, yield=84.2%) exhibited a sharp melting endotherm by differential scanning calorimetry (DSC) at 346° C. Also Fourier transform infrared (FTIR) analysis showed the following absorbances which are indicative of the structure for the final product: 3329 cm-1 (N-H stretch), 1528 cm-1 (Amide II band) and 1650 cm--1 (Amide I band). ##STR9##

Workup

  1. customas a reaction media
  2. customover a 30 minute
  3. additionDuring the course of this addition
  4. customa white precipitate is formed
  5. temperatureis maintained below 35° C.
  6. additionAfter the NAOH addition
  7. filtrationvacuum filtered (filtrate pH=7)
  8. customThe filter cake obtained
  9. washis washed with 400 ml of acetone
  10. additionadded to one liter of deionized water
  11. stirringstirred for 15 minutes
  12. filtrationfiltered
  13. washThis filter cake is washed with 500 ml of acetone
  14. customdried in a 105° C. vacuum oven to a constant weight

Sources & evidence

ORD record
ord-bc0ed7ddea2b4bb8a1c1d2d9f37b865c
Source dataset
uspto-grants-1993_11
Patent number
US05266661

Reaction notes

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