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 714609Notes

Reaction equation

HRID 714609 reaction equation
[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

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-17c0564c49dc45268a4ceaabb9c5bf19
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

Loading…