Diisopropylethylamine → HCID 22998459, Verbindung

HRID 1166957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166957
C(N(CC)C(C)C)(C)C.[CH3:10][C:11]1[C:15]([CH3:16])=[C:14]([NH:17][S:18]([C:21]2[CH:25]=[CH:24][S:23][CH:22]=2)(=[O:20])=[O:19])[O:13][N:12]=1.[CH3:26][Si:27]([CH3:34])([CH3:33])[CH2:28][CH2:29][O:30][CH2:31]Cl>C(Cl)Cl>[CH3:26][Si:27]([CH3:34])([CH3:33])[CH2:28][CH2:29][O:30][CH2:31][C:22]1[S:23][CH:24]=[CH:25][C:21]=1[S:18]([NH:17][C:14]1[O:13][N:12]=[C:11]([CH3:10])[C:15]=1[CH3:16])(=[O:19])=[O:20]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 22998511N-(3,4-dimethyl-5-isoxazolyl)thiophene-3-sulfonamide

Produkt 1

HCID 22998459HCID 22998459, VerbindungAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N,N-diisopropylethylamine (222 μl, 128 mmol) was added to a solution of N-(3,4-dimethyl-5-isoxazolyl)thiophene-3-sulfonamide (300 mg, 1.16 mmol) in methylene chloride (5 ml), and the mixture was stirred at room temperature for 15 min. The mixture was then cooled to 0° C. and 2-(trimethylsilyl)ethoxy methyl chloride (SEM chloride) (226 μl, 1.28 mmol) was added dropwise via syringe, and the resultant yellow solution was stirred at room temperature for 5 hours. Evaporation of solvents left an oil which was extracted into ethyl acetate, washed with water and brine solution and dried over magnesium sulfate. Flash chromatography of the residue using 10% ethyl acetate/hexanes yielded 321 mg 2-[2-(trimethylsilyl)ethoxymethyl]-N-(3,4-dimethyl-5-isoxazolyl)thiophene-3-sulfonamide as a clear colorless oil which solidified into a white solid upon standing (71% yield).

Aufarbeitung

  1. temperatureThe mixture was then cooled to 0° C.
  2. stirringthe resultant yellow solution was stirred at room temperature for 5 hours
  3. customEvaporation of solvents
  4. waitleft an oil which
  5. extractionwas extracted into ethyl acetate
  6. washwashed with water and brine solution
  7. dry with materialdried over magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-ec10c4d38f6747d79982900e0a17b4b4
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613804B2

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