Hydrochloric Acid → 1-(4-Hydroxyphenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

HRID 1616985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616985
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:19](=[O:20])[N:18]=[N:17][C:15]2=[O:16])=[CH:10][CH:9]=1.Cl>CC#N>[OH:7][C:1]1[CH:6]=[CH:5][C:4]([N:17]2[C:15](=[O:16])[N:14]([C:11]3[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=3)[C:19](=[O:20])[NH:18]2)=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 996PhenolHCID 779134-Phenyl-1,2,4-triazoline-3,5-dione

Produkt 1

HCID 672581691-(4-Hydroxyphenyl)-4-phenyl-1,2,4-triazolidine-3,5-dioneAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of phenol (11.3 mg, 0.120 mmol) in 100 mM pH 7.0 NaH2PO4/Na2HPO4 buffer (3.0 mL)-CH3CN (3.0 mL) was slowly dropped the 0.3 M solution of PTAD 17a (0.442 mL, 0.132 mmol) in CH3CN at room temperature. The resulting solution was stirred at room temperature for 30 minutes. The reaction mixture was acidified with 1M HCl and extracted with ethyl acetate twice. The organic layer was dried over Na2SO4 and concentrated in vacuo. The obtained crude material was purified by flash column chromatography (ethyl acetate) to give para-adduct 27 (4.8 mg, 15%) and para-ortho-di-adduct 27′ (10.1 mg, 19%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 11.35 (br, 1H), 9.60 (s, 1H), 7.53-7.35 (m, 7H), 6.83 (m, 2H), 13C NMR (75 MHz, DMSO-d6): δ 156.11, 152.73, 150.41, 132.22, 129.22, 128.78, 128.66, 127.19, 122.99, 116.22. HRMS: calcd for C14H11N3O3 (MH+) 270.0873. found 270.0873.

Aufarbeitung

  1. extractionextracted with ethyl acetate twice
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe obtained crude material
  5. customwas purified by flash column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-bfb3a288e50d49f6a258a63a18fbf492
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765920B2

Notizen zur Reaktion

Wird geladen…