Triethylamine → HCID 178486154, Verbindung

HRID 1942331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942331
[NH:1]1[CH:5]=[C:4]([S:6](Cl)(=[O:8])=[O:7])[N:3]=[CH:2]1.Cl.[CH3:11][NH:12][CH3:13].C(N(CC)CC)C>ClCCl>[CH3:11][N:12]([CH3:13])[S:6]([C:4]1[N:3]=[CH:2][NH:1][CH:5]=1)(=[O:8])=[O:7]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 178527435HCID 178527435, Verbindung

Produkt 1

HCID 178486154HCID 178486154, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1H-imidazole-4-sulfonyl chloride (0.5 g, 3.0 mmol; Matrix Scientific, Columbia, S.C.) in dichloromethane (10 mL) was added dimethylamine hydrochloride (0.245 g, 3.0 mmol) and triethylamine (1.3 mL, 9.0 mmol) at room temperature. The mixture was stirred for 16 hours at room temperature. TLC (petroleum ether/ethyl acetate=0:1) indicated the reaction was complete. The reaction mixture was washed with aq. ammonium chloride (30 mL) and extracted with dichloromethane: methanol=4:1 (3×50 mL). The combined organic phases were concentrated and precipitated from methanol to afford (I-35a) (0.36 g, 68.2%) as a white solid; 1H NMR (400 MHz, CD3OD): δ 7.74 (1 H), 7.61 (1 H), 2.68 (6 H).

Aufarbeitung

  1. washThe reaction mixture was washed with aq. ammonium chloride (30 mL)
  2. extractionextracted with dichloromethane
  3. concentrationThe combined organic phases were concentrated
  4. customprecipitated from methanol
  5. customto afford (I-35a) (0.36 g, 68.2%) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-2d276b9fa6574c078c881e215c8569c4
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389552B2

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