Water → 6-[(4-chlorophenyl)sulfanyl]-3-pyridinylamine

HRID 444461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444461
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+].O>[Fe].C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2800115HCID 2800115, Verbindung

Produkt 1

HCID 28001276-[(4-chlorophenyl)sulfanyl]-3-pyridinylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

6-(4-Chlorophenylthio)-3-nitropyridine (1.33 grams) was mixed with ammonium chloride (5.0 grams) in 5 ml. of water and about 50 ml. of 3A ethanol at 70°-80° C. Iron powder (3.0 grams) was added portionwise and the reaction mixture heated at 70°-80° C. with constant stirring, for 4 hours. The solution was filtered hot, solvents were removed, and the residue was washed with water; chloroform used to extract the compound was removed in vacuo. A thick oil was crystallized from ether-hexanes after passing through a flush with ethyl acetate on silica gel. The product precipitated as a white solid, yield 1.0 g., m.p. 55°-57°.

Aufarbeitung

  1. customat 70°-80° C
  2. temperaturethe reaction mixture heated at 70°-80° C. with constant stirring, for 4 hours
  3. filtrationThe solution was filtered hot
  4. customsolvents were removed
  5. washthe residue was washed with water
  6. extractionto extract the compound
  7. customwas removed in vacuo
  8. customA thick oil was crystallized from ether-hexanes
  9. customa flush with ethyl acetate on silica gel
  10. customThe product precipitated as a white solid, yield 1.0 g

Quellen und Nachweise

ORD-Eintrag
ord-7443d8a8676a4b9e9cd1821e6d452308
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04264605

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