3-Mercaptopropionic Acid → N-(4-Anilinophenyl)-3-sulfanylpropanamide

HRID 6192

Reaction equation

HRID 6192 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[SH:15][CH2:16][CH2:17][C:18](O)=[O:19].C1(C)C(C)=CC=CC=1>CCCCCC>[NH:7]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:18](=[O:19])[CH2:17][CH2:16][SH:15])=[CH:10][CH:9]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 65143-Mercaptopropionic AcidHCID 7237O-XyleneHCID 7564N-Phenyl-p-phenylenediamine

Product 1

HCID 19795022N-(4-Anilinophenyl)-3-sulfanylpropanamide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 18.4 grams of N-phenyl-p-phenylene diamine, 10.6 grams of β-mercaptopropionic acid and 120 milliliters of xylene (technical grade) was heated to reflux (about 140° C.) under nitrogen atmosphere, with stirring. A 1.6 milliliter quantity of water (90% of theory) was removed from this mixture by azetropic distillation through a Vigreux column with the aid of Dean-Start trap, during a 13-hour period. A solid product was isolated in 18.7 grams quantity from the reaction mixture by cooling the latter, pouring into hexane, collecting the resultant crystalline product by filtration, washing the crushed crystalline product with more hexane and evaporating to dryness. The product was recrystallized from hot toluene to 17.6 grams (64.5%) of white platelets melting at 98.3°-99.5° C. The resultant new compound, N-(4-anilino-phenyl)beta-mercaptopropionamide, sometimes referred to hereafter as MPDA, had mercaptan assay of 93.8% of theoretical, on the basis of a potentiometric titration with an isopropyl alcohol solution of silver nitrate, following a method described R. M. Pierson, A. J. Costanza and A. H. Weinstein, J. Polymer Sci., 17, 234 (1955).

Workup

  1. temperaturewas heated
  2. customA 1.6 milliliter quantity of water (90% of theory) was removed from this mixture by azetropic distillation through a Vigreux column with the aid of Dean-Start trap, during a 13-hour period
  3. customA solid product was isolated in 18.7 grams quantity from the reaction mixture
  4. temperatureby cooling the latter,
  5. customcollecting the resultant crystalline product
  6. filtrationby filtration
  7. washwashing the crushed crystalline product with more hexane
  8. customevaporating to dryness
  9. customThe product was recrystallized from hot toluene to 17.6 grams (64.5%) of white platelets melting at 98.3°-99.5° C

Sources & evidence

ORD record
ord-b17abff2b44840dd9b7ca02149e953e2
Source dataset
uspto-grants-1993_09
Patent number
US05247027

Linked notes

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