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Benzoyl Peroxide → 4-tert-Butyl-N-(3,4-dichloro-2-pyrazol-1-yl-phenyl)-benzenesulfonamide

HRID 502821
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 502821
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[N:22]2[CH:26]=[CH:25][CH:24]=[N:23]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:27]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:27])[C:16]=2[N:22]2[CH:26]=[CH:25][CH:24]=[N:23]2)(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 251347424-tert-butyl-N-(4-chloro-2-pyrazol-1-yl-phenyl)-benzenesulfonamide

Produkt 1

HCID 251352214-tert-Butyl-N-(3,4-dichloro-2-pyrazol-1-yl-phenyl)-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 25 mL scintillation vial was charged with 4-tert-butyl-N-(4-chloro-2-pyrazol-1-yl-phenyl)-benzenesulfonamide (synthesized according to general procedure D, 78 mg, 0.2 mmol), N-chlorosuccinimide (67 mg, 0.5 mmol), benzoyl peroxide (2.4 mg, 0.01 mmol), and carbon tetrachloride (4 mL). The vial was sealed and stirred for 18 hours at 80° C. The resultant solution was partitioned between ethyl acetate and water and the combined organics were washed with 1 N HCl, saturated sodium bicarbonate, and brine; dried over magnesium sulfate; filtered; and concentrated in vacuo. The crude product was subsequently purified by flash column chromatography (10-100% ethyl acetate in hexanes) followed by preparative HPLC (10-90% gradient of MeCN:water) to afford the title compound as a white solid: MS (ES) M+H expected 424.1, found 424.1.

Aufarbeitung

  1. customThe vial was sealed
  2. customThe resultant solution was partitioned between ethyl acetate and water
  3. washthe combined organics were washed with 1 N HCl, saturated sodium bicarbonate, and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationand concentrated in vacuo
  7. customThe crude product was subsequently purified by flash column chromatography (10-100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-73c4459f13cd4f26b3ddd154d55df8d8
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07776877B2

Notizen zur Reaktion

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