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4-tert-Butylbenzenesulfonamide → HCID 22282042, Verbindung

HRID 1368632
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1368632
[CH3:1][O:2][C:3]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([NH2:17])[N:5]([CH3:18])[N:4]=1.[C:19]([C:23]1[CH:28]=[CH:27][C:26]([S:29](N)(=[O:31])=[O:30])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(O)C.[OH-].[Na+].Cl>[C:19]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:17][C:6]2[N:5]([CH3:18])[N:4]=[C:3]([O:2][CH3:1])[C:7]=2[O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])(=[O:31])=[O:30])=[CH:25][CH:24]=1)([CH3:22])([CH3:20])[CH3:21]
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Komponenten

8

Edukt 2

HCID 2228724-tert-Butylbenzenesulfonamide2×HCID 22281998HCID 22281998, Verbindung

Produkt 1

HCID 22282042HCID 22282042, VerbindungAusbeute 33,6 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 313Hydrochloric AcidLösungsmittel
HCID 702
Ethanol
Lösungsmittel
HCID 1049PyridineLösungsmittel
HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 3-methoxy-4-(2-methoxyphenoxy)-1-methyl-1H-pyrazol-5-amine (Preparation 68) (45 mg), (4-tert-butyl)benzenesulfonamide (42 mg) and 4-dimethylaminopyridine (22 mg) in dry pyridine (2 ml) was stirred at room temperature for 16 hours. A further aliquot of (4-tert-butyl)benzenesulfonamide (42 mg) was added to the reaction mixture and stirring at room temperature was continued for a further 24 hours. The reaction mixture was diluted with ethanol (2 ml) and 1.0M aqueous sodium hydroxide solution (4 ml) and was then stirred at room temperature for 4 hours. The mixture was diluted with aqueous 1.0M hydrochloric acid (20 ml) and then extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with aqueous 1.0M hydrochloric acid (20 ml), dried (magnesium sulfate) and then concentrated under vacuum. The residue was purified by chromatography on silica (5 g) using 40% ethyl acetate/pentane as eluant to give the title compound as an off-white solid (27 mg), Rf 0.85 (ethyl acetate), m.p. 187.6° C.

Aufarbeitung

  1. stirringwas then stirred at room temperature for 4 hours
  2. extractionextracted with ethyl acetate (3×15 ml)
  3. washThe combined organic extracts were washed with aqueous 1.0M hydrochloric acid (20 ml)
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by chromatography on silica (5 g)

Quellen und Nachweise

ORD-Eintrag
ord-dcb053b6797a49d58799a8ec6cab2d7b
Quelldatensatz
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06573270B1

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