Dimethylamine → 5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(N,N-dimethylamidino)-4-trifluoromethylsulfinylpyrazole

HRID 429256

Reaction equation

HRID 429256 reaction equation
[NH2:1][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]=2Cl)[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([C:23]([F:26])([F:25])[F:24])=O.[CH3:27][NH:28][CH3:29].[OH2:30].[Cl-:31].[Na+]>O1CCOCC1.CCOCC.CO.C(OCC)(=O)C>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:31])=[CH:9][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19](=[NH:20])[N:28]([CH3:29])[CH3:27])[C:3]=1[S:21]([C:23]([F:26])([F:25])[F:24])=[O:30]

Participants

9

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 3352FipronilHCID 5234Sodium Chloride

Product 1

HCID 183547755-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(N,N-dimethylamidino)-4-trifluoromethylsulfinylpyrazoleYield 27%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole (0.97 g, 2.22 mmol) was dissolved in 10 ml of 1,4-dioxane and dimethylamine (50% aqueous solution) (1.20 ml, 11.4 mmol) was added, and then the mixture was stirred at room temperature for 5 days. After stirring, 20 ml of water and 20 ml of an aqueous saturated sodium chloride solution were added and the solution was extracted twice with 30 ml of ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off to obtain a yellow amorphous. The amorphous was subjected to silica gel column chromatography [eluent: mixed solvent of ethyl acetate and methanol (volume ratio=4:1)] and a small amount of ether was added to crystallize the resulting amorphous. This resultant was filtered to obtain 0.29 g (0.60 mmol) of the title compound as a colorless crystal. Yield 27%.

Workup

  1. stirringAfter stirring
  2. extractionthe solution was extracted twice with 30 ml of ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customto obtain a yellow amorphous
  6. customto crystallize the resulting amorphous
  7. filtrationThis resultant was filtered

Sources & evidence

ORD record
ord-0dfb01ce0f7c426f8def0d1255659a48
Source dataset
uspto-grants-2001_11
Patent number
US06316477B1

Linked notes

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