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Trifluoroacetic acid → 3-(8-Chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benzo[b]azepin-4-yl)acrylic Acid

HRID 2392566
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2392566
C([O:5][C:6]([CH:8]=[CH:9][C:10]1[C:11](=[O:25])[C:12]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:13]=2[NH:14][C:15](=[O:19])[C:16]=1[O:17][CH3:18])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.CO>[Cl:24][C:21]1[CH:22]=[CH:23][C:12]2[C:11](=[O:25])[C:10]([CH:9]=[CH:8][C:6]([OH:7])=[O:5])=[C:16]([O:17][CH3:18])[C:15](=[O:19])[NH:14][C:13]=2[CH:20]=1
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Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 540813424-[2-(Tert-butoxycarbonyl)ethenyl]-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine

Produkt 1

HCID 538847863-(8-Chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benzo[b]azepin-4-yl)acrylic AcidAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

4-[2-(Tert-butoxycarbonyl)ethenyl]-8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.3455 g) was dissolved in dry methylene chloride (7.5 mL) under argon. The solution was treated with trifluoroacetic acid (7 mL). The solution was stirred at room temperature for 30 minutes. The solution was concentrated under water aspirator vacuum and then it was dried under high vacuum to give a white solid. The solid was dissolved in 125 mL of hot methanol. The solution was filtered and concentrated to 80 mL volume as a white solid formed. It was cooled in an ice bath and the solid was filtered off, washed with cold methanol, and air-dried to give a white solid (0.162 g); mp 281.4°-282.0° C. (dec); 1H NMR (d6 -DMSO) 7.54 (d,1, J=16), 6.52 (d,1, J=16) for trans olefin protons; MS: m/z=308. Analysis for C14H10ClNO5 : Calculated: C, 54.65; H, 3.28; N, 4.55; Found: C, 54.36; H, 3.14; N, 4.37.

Aufarbeitung

  1. concentrationThe solution was concentrated under water
  2. customit was dried under high vacuum
  3. customto give a white solid
  4. filtrationThe solution was filtered
  5. concentrationconcentrated to 80 mL volume as a white solid
  6. customformed
  7. temperatureIt was cooled in an ice bath
  8. filtrationthe solid was filtered off
  9. washwashed with cold methanol
  10. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-c50e4e5978fe4cad81050d123f095105
Quelldatensatz
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05801168

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