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Potassium Carbonate → N-(2-Hydroxyethyl)-2-(2,4,6-trichlorophenylamino)-benzenesulfonamide

HRID 1259043
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1259043
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][CH2:12][CH2:13][OH:14])(=[O:10])=[O:9].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[C:17]=1Br.C([O-])([O-])=O.[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C(#N)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:14][CH2:13][CH2:12][NH:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:17]1[C:16]([Cl:15])=[CH:21][C:20]([Cl:22])=[CH:19][C:18]=1[Cl:23])(=[O:10])=[O:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 1405262-Bromo-1,3,5-trichlorobenzeneHCID 4587812-amino-N-(2-hydroxyethyl)benzenesulfonamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Produkt 1

HCID 42642465N-(2-Hydroxyethyl)-2-(2,4,6-trichlorophenylamino)-benzenesulfonamideAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a stirred solution of 2-Amino-N-(2-hydroxyethyl)-benzene sulfonamide (160 mg, 0.74 mmol), 1,3,5-trichloro-2-bromobenzene (241 mg, 0.93 mmol), K2CO3 (256 mg, 1.85 mmol) and xantphos (43 mg, 0.074 mmol) in acetonitrile (2 ml) under nitrogen in a microwave tube was added Pd2dba3 (34 mg, 0.037 mmol) in one portion and the tube sealed. The reaction was heated with stirring in a microwave at 160° C. for 120 minutes. The reaction was cooled before filtering through celite. The crude reaction mixture was part-purified by column chromatography eluting with ethyl acetate:hexane and the concentrated fractions further purified by preparative chromatography under acidic conditions to afford the named product (49.0 mg, 17%); δH (400 MHz, DMSO) 7.83 (3H, m), 7.75+7.45 (1H, d), 7.59+7.10 (1H, s), 7.55+7.38 (1H, t), 7.16+6.95 (1H, t), 7.10+6.40 (1H, d), 4.73 (1H, m), 3.35 (2H, m) and 2.83 (2H, m); LCMS Rt=7.92 min, m/z (ES+) 397 (M+H).

Aufarbeitung

  1. customthe tube sealed
  2. temperatureThe reaction was heated
  3. temperatureThe reaction was cooled
  4. filtrationbefore filtering through celite
  5. customThe crude reaction mixture
  6. customwas part-purified by column chromatography
  7. washeluting with ethyl acetate
  8. customhexane and the concentrated fractions further purified by preparative chromatography under acidic conditions

Quellen und Nachweise

ORD-Eintrag
ord-ea4575b722da458c80bc6ed6f4b9c37f
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466201B2

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