تفاعل #6288

ord-b17abff2b44840dd9b7ca02149e953e2

معادلة التفاعل

Nc1ccc(Nc2ccccc2)cc1
N-phenyl-p-phenylene diamine
O=C(O)CCS
β-mercaptopropionic acid
Cc1ccccc1C
xylene
O=C(CCS)Nc1ccc(Nc2ccccc2)cc1
N-(4-ANILINO-PHENYL)-β-MERCAPTOPROPIONAMIDE

الكواشف

لا شيء

المذيبات

ظروف التفاعل

درجة الحرارة
140°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةwas heated
  2. 2
    أخرىA 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. 3
    أخرىA solid product was isolated in 18.7 grams quantity from the reaction mixture
  4. 4
    درجة الحرارةby cooling the latter,
  5. 5
    أخرىcollecting the resultant crystalline product
  6. 6
    ترشيحby filtration
  7. 7
    غسيلwashing the crushed crystalline product with more hexane
  8. 8
    أخرىevaporating to dryness
  9. 9
    أخرىThe product was recrystallized from hot toluene to 17.6 grams (64.5%) of white platelets melting at 98.3°-99.5° C

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05247027uspto-grants-1993_09