Reaction equation
[CH2:1]([N:3]1[C:7]([OH:8])=[CH:6][CH:5]=[N:4]1)[CH3:2].[Cl:9][C:10]1[C:18]([C:19]2[N:23]([CH3:24])[N:22]=[C:21]([C:25]([CH3:27])=[O:26])[CH:20]=2)=[C:17]([Cl:28])[CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(#N)C>[Cl:9][C:10]1[C:18]([C:19]2[N:23]([CH3:24])[N:22]=[C:21]([C:25]([CH3:27])=[O:26])[CH:20]=2)=[C:17]([Cl:28])[CH:16]=[CH:15][C:11]=1[C:12]([O:8][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][CH:6]=1)=[O:13]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.21 g (1.9 mmol) of 1-ethyl-5-hydroxy-1H-pyrazole and 0.39 g (1.9 mmol) of N,N-dicyclohexylcarbodiimide were added to 0.59 g (1.9 mmol) of 2,4-dichloro-3-(1-methyl-3-methylcarbonyl-1H-pyrazol-5-yl)benzoic acid in 8 ml of acetonitrile. The mixture was stirred at room temperature for 12 hours and 25 ml of 5% strength sodium carbonate solution and 50 ml of ethyl acetate were added, insoluble components were filtered off and the organic phase was separated off, dried and concentrated. The residue was subsequently chromatographed over silica gel (eluent: ethyl acetate:cyclohexane=1:1). 0.21 g (27% of theory) of (1-ethylpyrazol-5-yl) 2,4-dichloro-3-(1-methyl-3-methylcarbonyl-1H-pyrazol-5-yl)benzoate was obtained.
Workup
- filtrationinsoluble components were filtered off
- customthe organic phase was separated off
- customdried
- concentrationconcentrated
- customThe residue was subsequently chromatographed over silica gel (eluent: ethyl acetate:cyclohexane=1:1)
Sources & evidence
- ORD record
- ord-01b944fcd4c8489082f50d481062d0ff
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06165944
Linked notes
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