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

HRID 444461Notes

Reaction equation

HRID 444461 reaction equation
[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

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2800115HCID 2800115, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-7443d8a8676a4b9e9cd1821e6d452308
Source dataset
uspto-grants-1981_04
Patent number
US04264605

Reaction notes

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