Trifluoroacetic acid → HCID 178434688, compound

HRID 47614

Reaction equation

HRID 47614 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14](CC3C=CC(OC)=CC=3)[N:13]=[C:12]([CH3:24])[C:11]=2[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:26])[CH:5]=[C:6]([Cl:8])[CH:7]=1.FC(F)(F)C(O)=O>>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[NH:14][N:13]=[C:12]([CH3:24])[C:11]=2[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:26])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22747490[5-(3,5-dichlorophenylthio)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

Product 1

HCID 178434688HCID 178434688, compoundYield 71.3%

Procedure

140 mg of [5-(3,5-dichlorophenylthio)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone was treated with 4 ml of trifluoroacetic acid. The solution was then heated at reflux for 2 h. The solvent was evaporated under reduced pressure. The residue was then partitioned between dichloromethane/saturated sodium hydrogen carbonate, washed with brine then dried over anhydrous magnesium sulphate, filtered and evaporated to give 75 mg of [5-(3,5-dichlorophenylthio)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone as a yellow solid which was used without further purification. Mass spectrum (ES) m/z 363[M+H]+.

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux for 2 h
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was then partitioned between dichloromethane/saturated sodium hydrogen carbonate
  5. washwashed with brine
  6. dry with materialthen dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-e9eeffe890ec4d609dcb2396330d5e76
Source dataset
uspto-grants-2004_03
Patent number
US06699887B2

Linked notes

Loading…