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Water → N-(2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)-2-nitrobenzenesulfonamide

HRID 1049423
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1049423
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=1[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.[N+:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[S:38](Cl)(=[O:40])=[O:39])([O-:31])=[O:30].O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:38]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N+:29]([O-:31])=[O:30])(=[O:39])=[O:40])=[CH:12][C:11]=1[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471Triethylamine2×HCID 155402-Nitrobenzenesulfonyl chloride2×HCID 1177600312'-Fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-amine

Produkt 1

HCID 117759909N-(2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)-2-nitrobenzenesulfonamideAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-amine (970 mg) in THF (34 mL) were added triethylamine (706 μL) and o-nitrobenzenesulfonyl chloride (823 mg) at 0° C., and the mixture was stirred at room temperature for 5 hr. Triethylamine (706 μL) and o-nitrobenzenesulfonyl chloride (374 mg) were further added at 0° C., and the mixture was stirred at room temperature for 20 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.31 g) as a yellow gummy substance.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 20 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-01557cc45fd941efaacebdab65eb629e
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09382188B2

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