Hydrochloric Acid → HCID 178470902, Verbindung

HRID 1057173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057173
Cl.[C:2]1(/[C:8](/[CH2:38][CH3:39])=[C:9](\[C:25]2[CH:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:27][CH:26]=2)/[C:10]2[CH:24]=[CH:23][C:13]3[N:14](C4CCCCO4)[N:15]=[N:16][C:12]=3[CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.C(OCC)(=O)C>[NH:14]1[C:13]2[CH:23]=[CH:24][C:10](/[C:9](/[C:25]3[CH:26]=[CH:27][C:28](/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][CH:30]=3)=[C:8](/[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)\[CH2:38][CH3:39])=[CH:11][C:12]=2[N:16]=[N:15]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 86695284(E)-Ethyl 3-(4-((E)-2-phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d][1,2,3]triazol-5-yl)but-1-en-1-yl)phenyl)acrylate

Produkt 1

HCID 178470902HCID 178470902, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Hydrochloric acid (2.7 mL, 2M in diethyl ether) was added to a solution of (E)-ethyl 3-(4-((E)-2-phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d][1,2,3]triazol-5-yl)but-1-en-1-yl)phenyl)acrylate (0.28 g, 0.55 mmol) in ethyl alcohol (27 mL) at room temperature, and the resulting mixture was heated at 70° C. for 2 h. The reaction was monitored by TLC. Upon completion, the mixture was cooled down to room temperature and concentrated to give a pale yellow solid. This solid was dissolved in ethyl acetate (100 mL), washed with saturated NaHCO3 (50 mL), water (100 mL) and brine (50 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated to give the crude product. This crude material was purified on a silica gel column eluted with 0-50% ethyl acetate in hexanes affording the title compound. LCMS: 424 (M+H)+.

Aufarbeitung

  1. temperatureUpon completion, the mixture was cooled down to room temperature
  2. concentrationconcentrated
  3. customto give a pale yellow solid
  4. washwashed with saturated NaHCO3 (50 mL), water (100 mL) and brine (50 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9982920574004adc8b03374cd467bfa7
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399646B2

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