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

HRID 1709011

反応式

HRID 1709011 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
140 °C

実験手順

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 azeotropic distillation through a Vigreux column with the aid of a Dean-Stark 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 by R. M. Pierson, A. J. Costanza and A. H. Weinstein, J. Polymer Sci., 17, 234 (1955).

後処理

  1. temperaturewas heated
  2. customA 1.6 milliliter quantity of water (90% of theory) was removed from this mixture by azeotropic distillation through a Vigreux column with the aid of a Dean-Stark 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

出典と根拠

ORDレコード
ord-83b16c235e1f4585930d2f34ed453726
出典データセット
uspto-grants-1990_08
特許番号
US04946905

関連ノート

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