Pyridine → 5-[4-(4-tert-Butyl-phenoxy)-phenylsulfamoyl]-2-methyl-benzoic acid

HRID 855986

Reaktionsgleichung

Reaktionsgleichung von HRID 855986
[C:1]([C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[S:20]([C:23]1[CH:24]=[CH:25][C:26]([CH3:32])=[C:27]([CH:31]=1)[C:28]([OH:30])=[O:29])(=[O:22])=[O:21].N1C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[C:1]([C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][S:20]([C:23]3[CH:24]=[CH:25][C:26]([CH3:32])=[C:27]([CH:31]=3)[C:28]([OH:30])=[O:29])(=[O:22])=[O:21])=[CH:14][CH:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 824984-(4-Tert-butylphenoxy)anilineHCID 3084495-(Chlorosulfonyl)-2-methylbenzoic acid

Produkt 1

HCID 589370405-[4-(4-tert-Butyl-phenoxy)-phenylsulfamoyl]-2-methyl-benzoic acidAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4-(4-tert-butyl-phenoxy)-phenylamine (0.1 g, 0.41 mmol). 5-chlorosulfonyl-2-methylbenzoic acid (0.097 g, 0.41 mmol) and pyridine (0.1 ml, 1.24 mmol) in 2 ml anhydrous tetrahydrofuran was heated at 60° C. for 2 hr. The reaction mixture was cooled to room temperature and diluted with 30 ml ethyl acetate. The ethyl acetate solution was washed sequentially with 25 ml 1N aqueous hydrochloric acid solution and 25 ml brine, dried (anhydrous sodium sulfate) and concentrated to dryness under reduced pressure. The crude product was purified by preparative thick layer chromatography (silica gel), eluting with 9:1 chloroform/methanol to yield the title compound.

Aufarbeitung

  1. washThe ethyl acetate solution was washed sequentially with 25 ml 1N aqueous hydrochloric acid solution and 25 ml brine
  2. dry with materialdried (anhydrous sodium sulfate)
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe crude product was purified by preparative thick layer chromatography (silica gel)
  5. washeluting with 9:1 chloroform/methanol

Quellen und Nachweise

ORD-Eintrag
ord-d16715c87bba49a5856bec6decc7aad8
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262318B2

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