Sodium hydride → 1-(2-chloro-4-trifluoromethoxyphenyl)-4-cyano-5-(N-propionyl-N-n-propylamino)pyrazole
Reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[N:7][N:8]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[Cl:26])[C:9]=1[NH:10][C:11](=[O:14])[CH2:12][CH3:13])#[N:4].[CH2:27](I)[CH2:28][CH3:29]>O1CCCC1>[C:3]([C:5]1[CH:6]=[N:7][N:8]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:23])([F:25])[F:24])=[CH:17][C:16]=2[Cl:26])[C:9]=1[N:10]([CH2:27][CH2:28][CH3:29])[C:11](=[O:14])[CH2:12][CH3:13])#[N:4]Participants
Procedure
0.8 g (0.033 mole) of sodium hydride is added to 10.8 g (0.03 mole) of 4-cyano-5-propionylamino-1-(2-chloro-4-trifluoromethoxyphenyl)-pyrazole in 100 ml of tetrahydrofuran and, when the evolution of gas has ended, 10.2 g (0.06 mole) of n-propyl iodide are added and the mixture is stirred at the reflux temperature for 48 hours. For working up, the mixture is concentrated in vacuo, the residue is taken up in 200 ml of methylene chloride and the mixture is washed twice with 100 ml of water each time, dried over sodium sulphate and concentrated in vacuo. The oil which remains is purified by column chromatography (eluant: chloroform/acetone 9:1) and crystallised from petroleum ether. 8.0 g (66.6% of theory) of 4-cyano-1-(2-chloro-4-trifluoromethoxyphenyl)-5-(N-n-propyl-N-propionylamino)-pyrazole of melting point 83° C. are obtained.
Workup
- concentrationthe mixture is concentrated in vacuo
- washthe mixture is washed twice with 100 ml of water each time
- dry with materialdried over sodium sulphate
- concentrationconcentrated in vacuo
- customThe oil which remains is purified by column chromatography (eluant: chloroform/acetone 9:1)
- customcrystallised from petroleum ether
Sources & evidence
- ORD record
- ord-8affe8faf11d4cd9800c154369146675
- Source dataset
- uspto-grants-1988_04
- Patent number
- US04740232
Reaction notes
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