Hydrochloric Acid → Methyl {3-(4-chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate

HRID 714609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714609
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@@H:14](O)[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[N:9]=2)=[CH:4][CH:3]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](/[CH:13]=[CH:14]/[C:15]([F:18])([F:16])[F:17])[C:11](=[O:20])[N:10]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[N:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 67749Trifluoromethanesulfonic anhydrideHCID 59536753Methyl {3-(4-chlorophenyl)-5-oxo-4-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate

Produkt 1

HCID 59536880Methyl {3-(4-chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

At RT, 5.0 g (13.12 mmol) of the compound from Example 8A together with 1.93 g (15.8 mmol) of 4-N,N-dimethylaminopyridine were initially charged in 70 ml of pyridine, 5.54 ml (32.92 mmol) of trifluoromethanesulfonic anhydride were added a little at a time and the mixture was stirred for 18 h. For work-up, 5 ml of 1 N hydrochloric acid were added and the pyridine was removed on a rotary evaporator. The residue was taken up in 50 ml of ethyl acetate and washed with 25 ml of water. The aqueous phase was re-extracted twice with in each case 25 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1, then 4:1). This gave 3.50 g (73% of theory) of the title compound.

Aufarbeitung

  1. customthe pyridine was removed on a rotary evaporator
  2. washwashed with 25 ml of water
  3. extractionThe aqueous phase was re-extracted twice with in each case 25 ml of ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by chromatography on silica gel (mobile phase

Quellen und Nachweise

ORD-Eintrag
ord-17c0564c49dc45268a4ceaabb9c5bf19
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187466B2

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