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Water → HCID 22176572, Verbindung

HRID 1797190
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1797190
[C:1](Cl)#[C:2][CH3:3].[NH2:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:28])([CH3:27])[CH2:19][NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1.C(N(CC)CC)C.[OH2:36]>C1COCC1>[F:28][C:18]([C:15]1[CH:14]=[CH:13][C:12]([C:8]2[CH:7]=[C:6]([NH:5][C:1](=[O:36])[CH2:2][CH3:3])[CH:11]=[CH:10][CH:9]=2)=[CH:17][CH:16]=1)([CH3:27])[CH2:19][NH:20][S:21]([CH:24]([CH3:25])[CH3:26])(=[O:23])=[O:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 244271-Chloroprop-1-yneHCID 9863239{2-[4-(3-Aminophenyl)phenyl]-2-fluoropropyl}[(methylethyl)sulfonyl]amine

Produkt 1

HCID 22176572HCID 22176572, VerbindungAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Into a 100 mL single-neck flask, 58 mg of propynyl chloride was added dropwise to 200 mg of {2-[4-(3-aminophenyl)phenyl]-2-fluoropropyl}[(methylethyl)sulfonyl]amine (prepared in example 5) and 63 mg of triethylamine in THF (25 mL) while stirring under a nitrogen atmosphere at room temperature. The reaction was allowed to stir at this temperature for 2 h. The mixture was then poured into H2O and the desired product was extracted into ethyl acetate. The organic layer was backwashed once with H2O, dried over K2CO3, and concentrated under reduced vacuum to yield 256 mg as a foam. This material was purified via silica gel chromatography employing the Chromatotron, using a 4000 micron rotor and eluting with a solvent of hexane/ethyl acetate 1:1 to yield the title compound (130 mg, 56%) as a white foam. Ion spray M.S. 405.5 (M*−1).

Aufarbeitung

  1. stirringto stir at this temperature for 2 h
  2. extractionthe desired product was extracted into ethyl acetate
  3. dry with materialdried over K2CO3
  4. concentrationconcentrated under reduced vacuum
  5. customto yield 256 mg as a foam
  6. customThis material was purified via silica gel chromatography
  7. washeluting with a solvent of hexane/ethyl acetate 1:1

Quellen und Nachweise

ORD-Eintrag
ord-0c94e115d3084589a8587d16394710f1
Quelldatensatz
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07034045B1

Notizen zur Reaktion

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