Potassium → HCID 15376176, compound

HRID 1421387Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:13])[C:9]([O:11][CH3:12])=[O:10].[K].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH:26]=[CH:25][C:24]([OH:27])=[N:23]2)=[CH:18][CH:17]=1>CS(C)=O>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH:26]=[CH:25][C:24]([O:27][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:8](=[O:13])[C:9]([O:11][CH3:12])=[O:10])=[N:23]2)=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 4.2 g of methyl 2-fluorophenylglyoxalate in 30 ml of anhydrous dimethyl sulfoxide was added dropwise to a solution of 5.0 g of the potassium salt of 1-(4-chlorophenyl)-3-hydroxy-pyrazole in 30 ml of anhydrous dimethyl sulfoxide. The batch was heated at 60° C. for 3.5 more hours, cooled and divided into two halves. One half was poured into ice-water/methyl tert-butyl ether for working-up. After the organic phase had been separated off, the aqueous phase was extracted three more times with methyl tert-butyl ether. The combined organic phases were dried over sodium sulfate and concentrated. The crude product was purified by chromatography over silica gel (eluent heptane/ethyl acetate 80/20→70/30). This gave 1.0 g of the title compound as a pale oil.

Workup

temperaturecooled
customAfter the organic phase had been separated off
extractionthe aqueous phase was extracted three more times with methyl tert-butyl ether
dry with materialThe combined organic phases were dried over sodium sulfate
concentrationconcentrated
customThe crude product was purified by chromatography over silica gel (eluent heptane/ethyl acetate 80/20→70/30)

Sources & evidence

ORD record: ord-2269476fac1d47fd92f86e5dd0c34ad2
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06075149

Reaction notes

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