2-methyl-N-[(1E)-1,3-oxazol-4-ylmethylidene]propane-2-sulfinamide → 2-Methyl-N-[1-(4-oxazolyl)ethyl]-2-propanesulfinamide

HRID 245899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245899
[O:1]1[CH:5]=[C:4](/[CH:6]=[N:7]/[S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])[N:3]=[CH:2]1.[CH3:14][Mg]Br>ClCCl>[O:1]1[CH:5]=[C:4]([CH:6]([NH:7][S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])[CH3:14])[N:3]=[CH:2]1

Komponenten

4

Edukt 2

HCID 894209892-methyl-N-[(1E)-1,3-oxazol-4-ylmethylidene]propane-2-sulfinamideHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 712881692-Methyl-N-[1-(4-oxazolyl)ethyl]-2-propanesulfinamideAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a round-bottomed flask, 2-methyl-propane-2-sulfinic acid 1-oxazol-4-yl-meth-(E)-ylideneamide (548 mg, 2.74 mmol) was dissolved in dichloromethane (9 ml). The reaction mixture was cooled to 0° C. and methylmagnesium bromide (3.0 M in diethyl ether, 1.0 ml, 3.0 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1 h then quenched with saturated aqueous NH4Cl and extracted with ethyl acetate (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to afford 588 mg of 2-methyl-propane-2-sulfinic acid (1-oxazol-4-yl-ethyl)-amide as a light yellow oil.

Aufarbeitung

  1. customthen quenched with saturated aqueous NH4Cl
  2. extractionextracted with ethyl acetate (2×)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-13b41da8a37245f79b4fba01f6a77073
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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