Methyl iodide → 2,6-dichloro-4-trifluoromethylphenyl-3-cyano-5-[N-(2-methoxyethyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole

HRID 2103412Notes

Reaction equation

HRID 2103412 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([NH:18][CH2:19][CH2:20][O:21][CH3:22])=[C:16]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])[C:15]([C:30]#[N:31])=[N:14]1.[H-].[Na+].I[CH3:35].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[C:17]([N:18]([CH2:19][CH2:20][O:21][CH3:22])[CH3:35])=[C:16]([S:23]([C:26]([F:29])([F:27])[F:28])(=[O:24])=[O:25])[C:15]([C:30]#[N:31])=[N:14]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 865999911-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-(2-methoxyethylamino)-4-trifluoromethylsulfonylpyrazole

Product 1

HCID 865999922,6-dichloro-4-trifluoromethylphenyl-3-cyano-5-[N-(2-methoxyethyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(2-methoxyethylamino)-4-trifluoromethylsulfonylpyrazole (1.5g, 2.9 mmol) in tetrahydrofuran at 20° C. under nitrogen, was added sodium hydride (0.38 g, 60% in oil, 9.4 mmol), and stirred for 0.5 hour. Iodomethane (1.68 g, 11.7 mmol) was added and the mixture stirred for 15 hours at 20° C., then heated to 40° C. for 8 hours. The mixture was added to ethyl acetate and saturated ammonium chloride solution. The organic layer was washed with water and brine, dried (sodium sulfate), evaporated and chromatographed on silica gel eluting with heptane-ethyl acetate (9:1) to give 1-(2,6-dichloro-4-trifluoromethylphenyl-3-cyano-5-[N-(2-methoxyethyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole as a white solid (Compound number 2-3, 0.78 g), mp 75° C.

Workup

  1. stirringthe mixture stirred for 15 hours at 20° C.
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. customevaporated
  5. customchromatographed on silica gel eluting with heptane-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-c839ba7c94c44b76b87489eace9a69f1
Source dataset
uspto-grants-2009_08
Patent number
US07576107B2

Reaction notes

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