Ammonium Chloride → HCID 68450007, Verbindung

HRID 511822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 511822
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9](/[CH:12]=[N:13]/[S@@:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])=[N:10][CH:11]=2)[CH2:3][CH2:2]1.[CH3:20][Mg]Br.[Cl-].[NH4+]>ClCCl>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([C@H:12]([NH:13][S@@:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])[CH3:20])=[N:10][CH:11]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 87457533HCID 87457533, VerbindungHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 68450007HCID 68450007, VerbindungAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of (R,E)-N-((5-(cyclopropylmethoxy)pyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide (6.2 g, 22 mmol) was dissolved into dichloromethane (110 ml). Methyl magnesium bromide (44 ml, 44 mmol, 1.0M in THF) was added to the mixture at −78° C. dropwise. The mixture was stirred for 1 h at −78° C. The mixture was poured into saturated ammonium chloride aqueous solution, and the aqueous phase was extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1 (v/v)) to give 3.2 g (49% yield) of the title compound as a white solid:

Aufarbeitung

  1. extractionthe aqueous phase was extracted with ethyl acetate (twice)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-7a1f22ecae234cd78cde8c82bf8c1b0f
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09101616B2

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