Potassium Chloride → HCID 178510672, compound
Reaction equation
C(C1C=CC=CC=1)C.Cl.CN(C)C(C)C.[Cl-].[K+].[F:18][C:19]([F:24])([F:23])[S:20](O)=[O:21].CN(C)C(C)C.S(Cl)(Cl)=O.[NH2:35][C:36]1[N:40]([C:41]2[C:46]([Cl:47])=[CH:45][C:44]([C:48]([F:51])([F:50])[F:49])=[CH:43][C:42]=2[Cl:52])[N:39]=[C:38]([C:53]#[N:54])[CH:37]=1>>[CH:45]1[C:44]([C:48]([F:51])([F:50])[F:49])=[CH:43][C:42]([Cl:52])=[C:41]([N:40]2[N:39]=[C:38]([C:53]#[N:54])[C:37]([S+:20]([O-:21])[C:19]([F:24])([F:23])[F:18])=[C:36]2[NH2:35])[C:46]=1[Cl:47]Participants
Reactant 7
Product 1
Conditions
- Temperature
- 0 °C
Procedure
A 500 ml jacketed reactor with stirrer, baffles and condenser was initially charged under a nitrogen atmosphere with 103 g of ethylbenzene, 6.3 g of dimethylisopropylamine hydrochloride (0.050 mol, 99%) and 15.5 g of potassium chloride (0.208 mmol). Subsequently, 31.5 g of trifluoromethanesulfinic acid (0.223 mol, 95.0%), 17.9 g of dimethylisopropylamine (0.203 mol, 99%) and 24.2 g of thionyl chloride (203 mmol, 99.7%) were metered in at 0° C. with cooling. After subsequently adding 54.8 g of 5-amino-3-cyano-1-(2,6-dichlor-4-trifluoromethylphenyl)pyrazole, the reaction mixture was stirred at 0° C. for 1 h, then heated to 35° C. over 45 min and stirred at 35° C. for a further 10 h. After the reaction had been quenched with sodium hydroxide solution and extracted with ethyl acetate and ethylbenzene, a nonisolated yield of fipronil of 80% was obtained in the crude solution (determination by means of quantitative HPLC).
Workup
- customwere metered in at 0° C.
- temperaturewith cooling
- temperatureheated to 35° C. over 45 min
- stirringstirred at 35° C. for a further 10 h
- customAfter the reaction had been quenched with sodium hydroxide solution
- extractionextracted with ethyl acetate and ethylbenzene
Sources & evidence
- ORD record
- ord-e423f6abb02d4fbc8e741ff52e893723
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354007B2
Reaction notes
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