Water → 4-hexyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide

HRID 631074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 631074
[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.[CH2:7]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O>N1C=CC=CC=1>[CH2:7]([C:13]1[CH:14]=[CH:15][C:16]([S:19]([NH:1][C:2]2[S:3][CH:4]=[N:5][N:6]=2)(=[O:21])=[O:20])=[CH:17][CH:18]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Komponenten

5

Edukt 3

HCID 962WaterHCID 199091,3,4-Thiadiazol-2-amineHCID 125827864-Hexylbenzene-1-sulfonyl chloride

Produkt 1

HCID 533223754-hexyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-amino-1,3,4-thiadiazole (2.0 g, 19.7 mmol) in pyridine (30 mL) under argon at −20° C. was added p-hexylbenzenesulfonyl chloride (5.48 g, 21 mmol) over 10 min. The reaction mixture was stirred at room temperature for 16 hours. Water (300 mL) was added to quench the reaction. The mixture was extracted with CH2Cl2 and the organic extracts washed with 2N HCl (2×150 mL), brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluted with methanol:DCM 1:33 to give the product (3.72 g, 11.4 mmol, 58% yield) as a solid, mp 125-126° C.; 1H NMR (300 MHz, CDCl3) δ 0.88 (t, 3H, J=7 Hz), 1.28 (m, 6H), 1.58 (m, 2H), 2.63 (t, 2H, J=7 Hz), 7.27 (d, 2H, J=8 Hz), 7.83 (d, 2H, J=8 Hz), 8.24 (s, 1H); 13C NMR (75 MHz, CDCl3) 14.1, 22.6, 28.9, 31.1, 31.6, 35.9, 126.5, 129.0, 138.1, 142.6, 148.6, 167.4; MS (Q-TOF) Calcd for C14H20N3O2S2 326.0997. found 326.0931 (M+H)+. Calcd for C14H19N3NaO2S2 348.0816. found 348.0816 (M+Na)+.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with CH2Cl2
  4. washthe organic extracts washed with 2N HCl (2×150 mL), brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluted with methanol:DCM 1:33

Quellen und Nachweise

ORD-Eintrag
ord-029cb75d073b467291ce670adaf83c42
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09320734B2

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