Methyl iodide → 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(3-ethylthiopropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole

HRID 2109915Notes

Reaction equation

HRID 2109915 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][CH2:21][S:22][CH2:23][CH3:24])=[C:16]([S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[C:15]([C:32]#[N:33])=[N:14]1.[H-].[Na+].I[CH3:37].[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][CH2:21][S:22][CH2:23][CH3:24])[CH3:37])=[C:16]([S:25]([C:28]([F:31])([F:30])[F:29])(=[O:26])=[O:27])[C:15]([C:32]#[N:33])=[N:14]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 866002281-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-(3-ethylthiopropylamino)-4-trifluoromethylsulfonylpyrazole

Product 1

HCID 866002291-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(3-ethylthiopropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazoleYield 57%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(3-ethylthiopropylamino)-4-trifluoromethylsulfonylpyrazole (2.0 g, 3.6 mmol) in tetrahydrofuran at 20° C. under nitrogen, was added sodium hydride (0.461 g, 60% in oil, 11.5 mmol), and stirred for 0.5 hour. Iodomethane (2.065 g, 14.4 mmol) was added and the mixture stirred for 4.5 hours at 20° C., then allowed to stand for 2.5 days. 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 (3:1) to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(3-ethylthiopropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole as a light brown solid (Compound number 2-14, 1.3 g, 57% yield), mp 89° C.

Workup

  1. stirringthe mixture stirred for 4.5 hours at 20° C.
  2. waitto stand for 2.5 days
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customchromatographed on silica gel eluting with heptane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-b39d6be940c44997b5a3e3e28a9c3890
Source dataset
uspto-grants-2009_04
Patent number
US07517877B2

Reaction notes

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