Hydrochloric Acid → HCID 18690740, compound

HRID 1871205Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8]C)=[CH:6][C:5]([C:10]2[C:14]([CH3:15])=[C:13]([S:16][CH3:17])[N:12]([CH3:18])[N:11]=2)=[C:4]([F:19])[CH:3]=1.[Cl-].[Li+].Cl>CN(C)C=O>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([C:10]2[C:14]([CH3:15])=[C:13]([S:16][CH3:17])[N:12]([CH3:18])[N:11]=2)=[C:4]([F:19])[CH:3]=1

Participants

Conditions

Temperature: 22 °C

Procedure

A mixture of 15 g (0.05 mol) of 3-(4-chloro-2-fluoro-5-methoxyphenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole (Example P7) and 10.6 g (0.25 mol) of lithium chloride in 100 ml of N,N-dimethylformamide is stirred at 22° C. in an argon atomsphere for 2.5 days. The solution is cooled and poured into 0.5 liter of ice-water and 15 ml of 37% hydrochloric acid and extracted with tert-butyl methyl ether (MTBE). The organic phase is extracted with a dilute sodium hydroxide solution, and the aqueous phase is separated off and again acidified and extracted with MTBE. AFter concentration by evaporation and recrystallisation in diethyl ether, 4.8 g (33.5% of the threoretical yield) of the desired product are obtained in the form of crystals having a melting point of 136-138° C. and 7.6 g of crude product of the desired compound in the form of an oil.

Workup

temperatureThe solution is cooled
extractionextracted with tert-butyl methyl ether (MTBE)
extractionThe organic phase is extracted with a dilute sodium hydroxide solution
customthe aqueous phase is separated off
extractionextracted with MTBE
concentrationAFter concentration
customby evaporation and recrystallisation in diethyl ether

Sources & evidence

ORD record: ord-2bc97683835c478b98d8f6b070ae7147
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06103667

Reaction notes

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