Potassium Iodide → 3-((4,5-Dichloro-2-nitrophenyl)amino)-1-propanol

HRID 354946

Reaktionsgleichung

Reaktionsgleichung von HRID 354946
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](Cl)=[CH:4][C:3]=1[Cl:12].[NH2:13][CH2:14][CH2:15][CH2:16][OH:17].[I-].[K+]>C(O)CCC>[Cl:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Komponenten

5

Edukt 3

HCID 4875Potassium IodideHCID 69832,4,5-TrichloronitrobenzeneHCID 90863-Amino-1-propanol

Produkt 1

HCID 1129553-((4,5-Dichloro-2-nitrophenyl)amino)-1-propanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 113.2 parts of 1,2,4-trichloro-5-nitrobenzene, 75 parts of 3-amino-1-propanol, 0.2 parts of potassium iodide and 200 parts of butanol is stirred and refluxed overnight. The butanol is removed by evaporation in vacuo and water is added to the residue. The product is extracted with 4-methyl-2-pentanone. The extract is washed a few times with water, dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is triturated in 2,2'-oxybispropane. The product is filtered off and crystallized from a mixture of 2,2'-oxybispropane and 2-propanol, yielding 3-[(4,5-dichloro-2-nitrophenyl)amino]-1-propanol; mp. 97° C.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. customThe butanol is removed by evaporation in vacuo and water
  3. additionis added to the residue
  4. extractionThe product is extracted with 4-methyl-2-pentanone
  5. washThe extract is washed a few times with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe oily residue is purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and 5% of methanol as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated
  13. customThe residue is triturated in 2,2'-oxybispropane
  14. filtrationThe product is filtered off
  15. customcrystallized from a mixture of 2,2'-oxybispropane and 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-6ecce55181bf40aea8691da2d0f839b3
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04377578

Verknüpfte Notizen

Wird geladen…