Acetic Acid → HCID 21188133, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][NH2:14].[C:15](O)(=O)[CH3:16]>C(O)C>[NH2:13][C:3]1[N:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:5][C:4]=2[Cl:12])[N:14]=[C:7]([C:15]2[CH:16]=[CH:8][CH:6]=[CH:5][CH:4]=2)[CH:2]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A solution of 2,6-dichloro-4-trifluoromethylphenylhydrazine (0.245 g) in ethanol (2 ml) was added to benzoylacetonotrile (0. 145 g) in ethanol (8 ml) and the solution heated at 80° C. for 6 hours. Glacial acetic acid (1 ml) was added and the mixture heated at 80° C. for 4 hours and then 90° C. for 2 hours. The reaction mixture was evaporated and the residue purified by column chromatography on silica gel (10 g) eluted with dichloromethane. Combination and evaporation of appropriate fractions followed by further purification of their residue by reverse phase high performance liquid chromatography on C18 silica eluted with methanol: acetonitrile: water (1:5:4). Combination and evaporation of appropriate fractions gave the title compound as a white solid m.p. 141.5-142.5° C.
Workup
- temperaturethe mixture heated at 80° C. for 4 hours
- customThe reaction mixture was evaporated
- customthe residue purified by column chromatography on silica gel (10 g)
- washeluted with dichloromethane
- customCombination and evaporation of appropriate fractions
- customfollowed by further purification of their residue by reverse phase high performance liquid chromatography on C18 silica
- washeluted with methanol: acetonitrile: water (1:5:4)
- customCombination and evaporation of appropriate fractions
Sources & evidence
- ORD record
- ord-634a5296aa8d405480934285bad699c8
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06255333B1
Reaction notes
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