Methyl Bromide → HCID 11214802, compound

HRID 2414445Notes

Reaction equation

[K].[Cl:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([Cl:13])[C:4]=1[N:14]1[C:18]([NH:19][C:20](=[O:25])[CH2:21][O:22][CH2:23][CH3:24])=[C:17]([S:26]([C:28]([F:31])([F:30])[F:29])=[O:27])[C:16]([C:32]#[N:33])=[N:15]1.[CH3:34]Br>C(#N)C>[Cl:13][C:5]1[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=[C:3]([Cl:2])[C:4]=1[N:14]1[C:18]([N:19]([CH3:34])[C:20](=[O:25])[CH2:21][O:22][CH2:23][CH3:24])=[C:17]([S:26]([C:28]([F:31])([F:29])[F:30])=[O:27])[C:16]([C:32]#[N:33])=[N:15]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of the potassium salt of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-5-(ethoxyacetamido)pyrazole, prepared in Step 1 above, (18.9 g, assay=75.6%, 0.026 mol) in 56.8 g of acetonitrile, a solution of methyl bromide in acetonitrile (86.5 g, conc=28%, 0.255 mol) was added. The mixture was stirred during 6 hours at 60° C. and then concentrated to dryness. The residue was solubilized in a mixture of toluene (100 g) and water (100 g). The organic layer was washed with 100 g of water and concentrated to a 38% solution, heated to 80° C. and product was recrystallized in a 40/60 toluene/n-heptane solution to afford 10.3 g of a white solid (yield=64%, assay=85%).

Workup

customprepared in Step 1 above
concentrationconcentrated to dryness
additionThe residue was solubilized in a mixture of toluene (100 g) and water (100 g)
washThe organic layer was washed with 100 g of water
concentrationconcentrated to a 38% solution
temperatureheated to 80° C.
customproduct was recrystallized in a 40/60 toluene/n-heptane solution

Sources & evidence

ORD record: ord-f64614cc93e24e0fadd4140261a5549a
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812347B2

Reaction notes

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