Dimethylamine → 5-Amino-1-(2-chloro-6-dimethylamino-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole

HRID 253524Notes

Reaction equation

HRID 253524 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12](Cl)=[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][NH:29][CH3:30].CCCCCCC.C(OCC)(=O)C.O>O1CCOCC1>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([N:29]([CH3:30])[CH3:28])=[CH:11][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([C:24]([F:25])([F:27])[F:26])(=[O:22])=[O:23]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 3078139Fipronil sulfoneHCID 21899848Ethylacetate heptane

Product 1

HCID 114880375-Amino-1-(2-chloro-6-dimethylamino-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
200 °C

Procedure

To a mixture of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole (0.5 g, 1.1 mmol) in dioxan (5 ml) was added dimethylamine (aqueous solution 60%, 0.33 g, 4.4 mmol). The mixture was heated at 200° C. for 30 min in the microwave oven (Smith Synthesizer) under pressure. After extractive workup (heptane-ethyl acetate, water) and column chromatography the title product was obtained (0.18 g), mp 197° C., 1H-NMR: 2.75 (6H), 6.27 (2H), 7.13 and 7.24 (2H); 19F-NMR: −64.0, −80.6.

Sources & evidence

ORD record
ord-ca0df0d08a2648fe86a1b8c34a2f5b1b
Source dataset
uspto-grants-2011_01
Patent number
US07872038B2

Reaction notes

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