Hydrochloric Acid → HCID 178440858, Verbindung

HRID 1057174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057174
[Li+].[OH-].[NH:3]1[C:7]2[CH:8]=[CH:9][C:10](/[C:12](/[C:22]3[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([O:32]CC)=[O:31])=[CH:24][CH:23]=3)=[C:13](/[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)\[CH2:14][CH3:15])=[CH:11][C:6]=2[N:5]=[N:4]1.Cl>C1COCC1.CCO.O>[NH:3]1[C:7]2[CH:8]=[CH:9][C:10](/[C:12](/[C:22]3[CH:23]=[CH:24][C:25](/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31])=[CH:26][CH:27]=3)=[C:13](/[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)\[CH2:14][CH3:15])=[CH:11][C:6]=2[N:5]=[N:4]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178470902HCID 178470902, Verbindung

Produkt 1

HCID 178440858HCID 178440858, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21873804Tetrahydrofuran ethanolLösungsmittel

Versuchsvorschrift

An aqueous solution of LiOH (0.22 g, 9.4 mmol) was added to a solution of (E)-ethyl 3-(4-((E)-1-(1H-benzo[d][1,2,3]triazol-5-yl)-2-phenylbut-1-en-1-yl)phenyl)acrylate (0.2 g, 0.47 mmol) in THF-EtOH (1:1, 24 mL) at room temperature, and the resulting mixture was stirred overnight. The reaction was monitored by LCMS. Upon completion, 1N aqueous HCl was added until the pH was 3. Then, the mixture was diluted with water and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with water (100 mL), washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated to give the crude product. This crude material was purified on a silica gel column eluted with 0-20% methanol in dichloromethane affording the title compound as an off-white solid (0.12 g). 1H NMR (300 MHz, DMSO-d6): δ 15.65 (br, 1H), 12.29 (br, 1H), 7.92 (d, 1H), 7.78 (s, 1H), 7.48-7.35 (m, 3H), 7.24-7.13 (m, 7H), 6.91 (d, 2H), 6.37 (d, 1H), 2.39 (q, 2H), 0.89 (t, 3H); LCMS: 396 (M+H)+.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers were washed with water (100 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c22857e210204446b344bac729af8c01
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399646B2

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