Hydrochloric Acid → HCID 136387778, Verbindung

HRID 2402909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2402909
C([S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[CH:8][C:7]=1[C:19]([F:22])([F:21])[F:20])(C)(C)C.[ClH:23]>>[ClH:23].[CH3:18][C:14]1[CH:13]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([SH:5])=[C:7]([C:19]([F:22])([F:20])[F:21])[CH:8]=2)[CH:17]=[CH:16][N:15]=1

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 86684913HCID 86684913, Verbindung

Produkt 1

HCID 136387778HCID 136387778, VerbindungAusbeute 93,9 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-(4-tert-Butylsulfanyl-3-trifluoromethyl-phenyl)-2-methyl-pyridine (65.1 g, ˜200 mmol) was dissolved in 5 M HCl (800 mL) and the yellowish solution was warmed up and stirred at 100° C. under reflux for 22 h. After cooling (˜1 h) and stirring at room temperature for 0.5 h, the beige suspension was filtered and the filter cake was washed with deionized water (400 mL) and acetone (200 mL) and then dried (50° C./≧10 mbar/24 h) to give 57.4 g (93.9%) of the title compound as an off-white, crystalline powder, mp. >270° C. (dec.). 1H NMR (CDCl3+2 drops TFA, 400 MHz) δ 2.96 (s, 3H), 4.06 (q, J=3.3 Hz, 1H), 7.63 (d, J=8.3 Hz, 1H), 7.74 (dd, J1=8.3 Hz, J2=2.1 Hz, 1H), 7.84 (d, J=1.9 Hz, 1H), 7.93 (dd, J1=6.3 Hz, J2=1.9 Hz, 1H), 7.97 (d, J=1.9, 1H), 8.79 (d, J=6.2 Hz, 1H), 9.96 (s, 14H, TFA), 15.18 (br s, 1H). ESI-MS (m/z) [M−HCl]− 270 (100).

Aufarbeitung

  1. temperaturethe yellowish solution was warmed up
  2. temperatureunder reflux for 22 h
  3. temperatureAfter cooling (˜1 h)
  4. stirringstirring at room temperature for 0.5 h
  5. filtrationthe beige suspension was filtered
  6. washthe filter cake was washed with deionized water (400 mL) and acetone (200 mL)
  7. customdried (50° C./≧10 mbar/24 h)

Quellen und Nachweise

ORD-Eintrag
ord-da49306c2c6e4ce3a10ff6ffc018a6e6
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796471B2

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