Pyridine → HCID 18690747, compound

HRID 1871206Notes

Reaction equation

N1C=CC=CC=1.FC(F)(F)S([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])(=O)=O.[Cl:22][C:23]1[C:28](O)=[CH:27][C:26]([C:30]2[C:34]([CH3:35])=[C:33]([S:36][CH3:37])[N:32]([CH3:38])[N:31]=2)=[C:25]([F:39])[CH:24]=1>O1CCOCC1>[Cl:22][C:23]1[C:28]([O:12][S:13]([C:16]([F:17])([F:18])[F:19])(=[O:14])=[O:15])=[CH:27][C:26]([C:30]2[C:34]([CH3:35])=[C:33]([S:36][CH3:37])[N:32]([CH3:38])[N:31]=2)=[C:25]([F:39])[CH:24]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

65 ml (0.8 mol) of pyridine and then 80 ml (0.48 mol) of trifluoromethanesulfonic acid anhydride are added dropwise at 0-5° C. to a solution of 129 g (0.3 mol) of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole (approx. 70%) (Example P9) in 1.2 liters of 1,4-dioxane. After being stirred for 30 minutes at 0-5° C. and then at 22° C. overnight, the reaction mixture is concentrated to approximately 1/3 of its original volume by evaporation, poured into a mixture of ice, water and hydrochloric acid, extracted with MTBE, washed with water and concentrated by evaporation. After purification of the crude product by silica gel chromatography, 87.7 g (70% of the theoretical yield) of the desired compound are isolated in the form of crystals having a melting point of 54-56° C.

Workup

concentrationat 22° C. overnight, the reaction mixture is concentrated to approximately 1/3 of its original volume by evaporation
additionpoured into a mixture of ice, water and hydrochloric acid
extractionextracted with MTBE
washwashed with water
concentrationconcentrated by evaporation
customAfter purification of the crude product by silica gel chromatography, 87.7 g (70% of the

Sources & evidence

ORD record: ord-3ee0049e92b54d1cb5c7b5e05f0f6f50
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06103667

Reaction notes

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