Dimethylformamide → 5-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzamide

HRID 1386299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1386299
Cl.[CH3:2][O:3][C:4]1[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:6][C:7]([N+:13]([O-:15])=[O:14])=[C:8]([CH:12]=1)[C:9](O)=[O:10].C[N:26](C=O)C>S(Cl)(Cl)=O>[CH3:2][O:3][C:4]1[C:5]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:6][C:7]([N+:13]([O-:15])=[O:14])=[C:8]([CH:12]=1)[C:9]([NH2:26])=[O:10]

Komponenten

4

Edukt 2

HCID 6228DimethylformamideHCID 684411845-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochloride

Produkt 1

HCID 218748225-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzamideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A solution of 5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochloride (9.63 g, 24 mmol) in thionyl chloride (20ml) and DMF (50 μl) was heated at 45° C. for 1.5 hours. The excess thionyl chloride was removed by evaporation and by azeotroping with toluene (×2). The resulting solid was suspended in THF (250 ml) and methylene chloride (100 ml) and ammonia was bubbled though the mixture for 30 minutes and the mixture stirred for a further 1.5 hours at ambient temperature. The volatiles were removed by evaporation, the residue was dissolved in water and applied to a Diaion (trade mark of Mitsubishi) HP20SS resin column and eluted with water/methanol (100/0 to 95/5). The solvent was removed by evaporation from the fractions containing product and the residue was dissolved in a minimum of methanol and the solution was diluted with ether. The resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 5-methoxy-2-nitro4-(3-(pyrrolidin-1-yl)propoxy)benzamide (7.23 g, 73%).

Aufarbeitung

  1. customThe excess thionyl chloride was removed by evaporation
  2. customby azeotroping with toluene (×2)
  3. custommethylene chloride (100 ml) and ammonia was bubbled though the mixture for 30 minutes
  4. customThe volatiles were removed by evaporation
  5. dissolutionthe residue was dissolved in water
  6. washeluted with water/methanol (100/0 to 95/5)
  7. customThe solvent was removed by evaporation from the fractions
  8. additioncontaining product
  9. dissolutionthe residue was dissolved in a minimum of methanol
  10. additionthe solution was diluted with ether
  11. filtrationThe resulting precipitate was collected by filtration
  12. washwashed with ether
  13. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-658b798a6e92484cad5e442dd30f7bba
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265411B1

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