p-Toluenesulfonic acid → 4-Chloro-3-[4-chloro-3-(1,3-dithian-2-yl)-phenyl]-5-difluoromethoxy-1-methyl-1H-pyrazole

HRID 583040Notes

Reaction equation

[CH2:1]([SH:5])[CH2:2][CH2:3][SH:4].[Cl:6][C:7]1[C:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([CH:24](OC)OC)[CH:18]=2)=[N:9][N:10]([CH3:16])[C:11]=1[O:12][CH:13]([F:15])[F:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:6][C:7]1[C:8]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([CH:24]3[S:5][CH2:1][CH2:2][CH2:3][S:4]3)[CH:18]=2)=[N:9][N:10]([CH3:16])[C:11]=1[O:12][CH:13]([F:14])[F:15]

Participants

Conditions

Temperature: 65 °C

Procedure

0.5 g (4.6 mmol) of 1,3-propanedithiol was added to a solution of 1.7 g (4.6 mmol) of 4-chloro-3-[4-chloro-3-(dimethoxymethyl)phenyl]-5-difluoromethoxy-1-methyl-1H-pyrazole in 50 ml of toluene. The mixture was heated to 60-70° C. and then a spatula-tipful of p-toluenesulfonic acid was added. The reaction mixture was stirred at reflux temperature for 3 hours and then cooled and diluted with 50 ml of toluene. The organic phase was washed with 10% strength by weight sodium hydrogen carbonate solution and water and then dried over magnesium sulfate and concentrated. The crude product thus obtained was purified by chromatography on silica gel (eluent: hexane/ethyl acetate=4:1). Yield: 1.8 g.

Workup

temperatureat reflux temperature for 3 hours
temperaturecooled
washThe organic phase was washed with 10% strength by weight sodium hydrogen carbonate solution and water
dry with materialdried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-2471a6651c3740d2918754167d966a0f
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05928999

Reaction notes

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