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Hydrochloric Acid → 4-hexadecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide

HRID 1966915
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1966915
[CH2:1]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[S:27]1[CH:31]=[N:30][N:29]=[C:28]1[NH2:32].Cl>N1C=CC=CC=1>[CH2:1]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:32][C:28]2[S:27][CH:31]=[N:30][N:29]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 199091,3,4-Thiadiazol-2-amineHCID 20570237p-Hexadecylbenzenesulfonyl chloride

Produkt 1

HCID 529388554-hexadecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of p-hexadecylbenzenesulfonyl chloride (600 mg, 1.50 mmol) in pyridine (8 mL) was added 1,3,4-thiadiazol-2-amine (228 mg, 2.25 mmol). The reaction mixture was stirred at room temperature for 6 hours, then 2 M HCl (40 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×50 mL), the organic layer was washed with water (40 mL) and brine (40 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by chromatography over silica gel (70-230 mesh) eluted with methanol:DCM 1:19 to give the product as a solid (320 mg, 0.69 mmol, 46% yield), mp 118-119° C.; 1H NMR (300 MHz, CDCl3) δ 0.88 (t, 3H, J=6.9 Hz), 1.25 (m, 26H), 1.59 (m, 2H), 2.64 (t, 2H, J=8.1 Hz), 7.29 (d, 2H, J=7.8 Hz), 7.84 (d, 2H, J=7.8 Hz), 8.23 (s, 1H); 13C NMR (75 MHz, CDCl3) 14.1, 22.7, 29.2, 29.3, 29.4, 29.6, 29.7, 31.1, 31.9, 35.9, 126.5, 128.9, 138.1, 142.5, 148.7, 167.5; MS (LCQ, ESI+) Calcd for C24H40N3O2S2 466.3, found 466.3 (M+H)+; HRMS (ESI+, m/z) Calcd for C24H40N3O2S2 466.2556, found 466.2558 (M+H)+.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. washthe organic layer was washed with water (40 mL) and brine (40 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography over silica gel (70-230 mesh)
  8. washeluted with methanol:DCM 1:19

Quellen und Nachweise

ORD-Eintrag
ord-67b5c2020fa54e7e9ede20694a6cbf7d
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08420678B2

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