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

HRID 1172107Notes

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-b511b0ec2d1a48a0a3e96c4b48d7ed1b
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07833939B2

Reaction notes

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