Hydrochloric Acid → 4-chloromethyl-3-methoxy-1-methyl-5-trifluoromethyl-1H-pyrazole

HRID 1292800Notes

Reaction equation

[CH2:1]=[O:2].[ClH:3].CO[C:6]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:8]([CH3:15])[N:7]=1.[C:16](=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O>[Cl:3][CH2:6][C:10]1[C:1]([O:2][CH3:16])=[N:7][N:8]([CH3:15])[C:9]=1[C:11]([F:12])([F:13])[F:14]

Participants

Conditions

Temperature: 80 °C

Procedure

0.45 g of paraformaldehyde (15.0 mmoles in terms of formaldehyde) and 5 ml of concentrated hydrochloric acid were added to a solution of 1.00 g (5.6 mmoles) of 3-methoxy-1-methyl-5-trifluoromethyl-1H-pyrazole dissolved in 25 ml of acetic acid. The mixture was stirred at 80° C. for 2 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water and neutralized with potassium carbonate, followed by extraction with ethyl acetate. The resulting organic layer was washed with water and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 0.83 g (yield: 65.0%) of 4-chloromethyl-3-methoxy-1-methyl-5-trifluoromethyl-1H-pyrazole.

Workup

customto give rise
customto a reaction
customAfter the completion of the reaction
extractionfollowed by extraction with ethyl acetate
washThe resulting organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationThe resulting solution was subjected to vacuum distillation
customto remove the solvent
customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent)

Sources & evidence

ORD record: ord-f1765de6a27744edbd1f4acda387a121
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238689B2

Reaction notes

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