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Hydrochloric Acid → N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-dodecylbenzenesulfonamide

HRID 631048
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 631048
[NH2:1][C:2]1[S:3][C:4]([C:7]([CH3:10])([CH3:9])[CH3:8])=[N:5][N:6]=1.[CH2:11]([C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl>N1C=CC=CC=1>[C:7]([C:4]1[S:3][C:2]([NH:1][S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:24][CH:25]=2)(=[O:31])=[O:30])=[N:6][N:5]=1)([CH3:10])([CH3:9])[CH3:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 1042154-Dodecylbenzenesulfonyl chlorideHCID 170170Buthidazolamine

Produkt 1

HCID 53318406N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-dodecylbenzenesulfonamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

2-Amino-5-tert-butyl-1,3,4-thiadiazole (204 mg, 1.3 mmol) was suspended in pyridine (0.5 mL). p-Dodecylbenzenesulfonyl chloride (300 mg, 0.87 mmol) was added slowly at 0° C. The reaction mixture was then heated to 95° C. and was stirred at this temperature for 1 h. The reaction mixture was then added to aqueous 10% HCl (5 mL) and the resulting mixture extracted with ethyl acetate (3×10 mL). The organic extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered, and volatiles evaporated to yield a solid mass. Chromatography on silica gel (70-230 mesh) eluted with 2% MeOH in CH2Cl2 gave the product (350 mg, 0.75 mmol, 87%). Recrystallization from hexanes:ethyl acetate (3:7) gave an analytical sample, mp 117-118° C.; 1H NMR (500 MHz, CDCl3) δ 0.88 (3, t, J=6.5 Hz), 1.20-1.36 (18, m), 1.38 (9, s), 1.56-1.64 (2, m), 2.63 (2, t, J=7.5 Hz), 7.25 (2, d, J=8.0 Hz), 7.86 (2, d, J=8.0 Hz), 12.24 (1, br s); 13C NMR (125 MHz, CDCl3) δ 14.1, 22.7, 29.2, 29.3, 29.4, 29.5, 29.6, 29.7, 31.1, 31.8, 35.8, 36.5, 126.5, 128.7, 138.5, 148.1, 167.8, 168.0; MS (ESI+, m/z) Calcd for C24H40N3O2S2 466.3. found 466.2 (M+H)+. HRMS (ESI+, m/z) Calcd for C24H40N3O2S2 466.2562. found 466.2562 (M+H)+.

Aufarbeitung

  1. extractionthe resulting mixture extracted with ethyl acetate (3×10 mL)
  2. washThe organic extracts were washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customvolatiles evaporated
  6. customto yield a solid mass
  7. washChromatography on silica gel (70-230 mesh) eluted with 2% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-2c46518e56664b4e922e70497db184c5
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09320734B2

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