Water → 1-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-(3-ethylthiopropylamino)-4-trifluoromethylsulfonylpyrazole

HRID 2109914Notes

Reaction equation

HRID 2109914 reaction equation
Br[C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22].[CH2:28]([S:30][CH2:31][CH2:32][CH2:33][NH2:34])[CH3:29].C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.CN(C)C=O.ClCCl>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]([NH:34][CH2:33][CH2:32][CH2:31][S:30][CH2:28][CH3:29])=[C:3]([S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])[C:4]([C:19]#[N:20])=[N:5]1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 167270545-Bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazoleHCID 214853303-(Ethylsulfanyl)propan-1-amine

Product 1

HCID 866002281-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-(3-ethylthiopropylamino)-4-trifluoromethylsulfonylpyrazoleYield 86%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 5-bromo-1(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole (5.0 g, 9.7 mmol) in 1,4-dioxane (20 ml) and N,N-dimethylformamide (20 ml) was added 3-ethylthiopropylamine (2.306 g, 19.3 mmol) and potassium carbonate (2.7 g, 19.3 mmol). The resulting mixture was stirred at 20° C. for 2.75 hours, left to stand overnight, then poured into a mixture of water and dichloromethane. The organic phase was washed with water, dried (sodium sulfate), evaporated and chromatographed on silica gel, eluting with heptane-ethyl acetate (4:1) to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(3-ethylthiopropylamino)-4-trifluoromethylsulfonylpyrazole as a yellow solid (Compound number 1-14, 4.79 g, 86% yield), mp 80° C.

Workup

  1. waitleft
  2. waitto stand overnight
  3. washThe organic phase was washed with water
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customchromatographed on silica gel
  7. washeluting with heptane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-27071b5661864f0490cb41baa33c5c9c
Source dataset
uspto-grants-2009_04
Patent number
US07517877B2

Reaction notes

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