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

HRID 2103411Notes

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].[CH3:28][O:29][CH2:30][CH2:31][NH2:32].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:32][CH2:31][CH2:30][O:29][CH3:28])=[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

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole (2.5 g, 4.8 mmol) in 1,4-dioxane and N,N-dimethylformamide was added 2-methoxyethylamine (0.74 g, 9.7 mmol) and potassium carbonate (1.35 g, 9.7 mmol). The resulting mixture was stirred at 50° C. for 4 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. The crude product was recrystallised from diisopropylether to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(2-methoxyethylamino)4-trifluoromethylsulfonylpyrazole as a white solid (Compound number 1-3, 1.30 g), mp 164° C.

Workup

waitleft
waitto stand overnight
washThe organic phase was washed with water
dry with materialdried (sodium sulfate)
customevaporated
customThe crude product was recrystallised from diisopropylether

Sources & evidence

ORD record: ord-3940b18768c54839b3e82b539ac291fe
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576107B2

Reaction notes

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