Tributylamine → Isobutyl 2-hydroxy-5-[2-[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoate

HRID 1464162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1464162
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:16])=[C:7]([CH:15]=1)[C:8]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[O:9])=[CH2:2].I[C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][N:29]=2)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(N(CCCC)CCCC)CCC>[Pd].CC(N(C)C)=O>[OH:16][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[CH:2][C:18]2[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]3[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][N:29]=3)(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:15][C:7]=1[C:8]([O:10][CH2:11][CH:12]([CH3:13])[CH3:14])=[O:9]

Komponenten

6

Edukt 3

HCID 7622TributylamineHCID 37926154-iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamideHCID 19423382Isobutyl 5-ethenyl-2-hydroxybenzoate

Produkt 1

HCID 54356729Isobutyl 2-hydroxy-5-[2-[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoateAusbeute 51,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

10% Palladium on charcoal (0.5g) was added to a solution of isobutyl 5-ethenyl-2-hydroxybenzoate (6.6 g, 30mmol) and 4-iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamide (11.2 g, 30 mmol) in dimethylacetamide (10 ml) and tributylamine (10 ml, 42 mmol) at 110° C. After 90 min. the solution was filtered and diluted with isopropanol (0.3 l) and chilled in a freezer. The product was filtered off, dried and dissolved in boiling formic acid (100 ml). The solution was filtered and water (65 ml) was added. After cooling to refrigerator temperature the product was filtered off and dried to yield 7.2 g (51%) product

Aufarbeitung

  1. filtrationAfter 90 min. the solution was filtered
  2. additiondiluted with isopropanol (0.3 l)
  3. temperaturechilled in a freezer
  4. filtrationThe product was filtered off
  5. customdried
  6. dissolutiondissolved
  7. filtrationThe solution was filtered
  8. additionwater (65 ml) was added
  9. temperatureAfter cooling to refrigerator temperature the product
  10. filtrationwas filtered off
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-87e8454b11784379b44bdfe542a751f5
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05302718

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