Hydrochloric Acid → 5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(1,2,4-oxadiazol-3-yl)-4-trifluoromethylsulfinylpyrazole

HRID 429266Notes

Reaction equation

HRID 429266 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]([N:18]=COC)=[C:16]([S:22]([C:24]([F:27])([F:26])[F:25])=[O:23])[C:15]([C:28]2[N:32]=[CH:31][O:30][N:29]=2)=[N:14]1.Cl.O.C(=O)([O-])O.[Na+]>CC(C)=O>[NH2:18][C:17]1[N:13]([C:3]2[C:4]([Cl:12])=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=2[Cl:1])[N:14]=[C:15]([C:28]2[N:32]=[CH:31][O:30][N:29]=2)[C:16]=1[S:22]([C:24]([F:27])([F:26])[F:25])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid3×HCID 962WaterHCID 516892Sodium BicarbonateHCID 570711311-(2,6-Dichloro-4-trifluoromethylphenyl)-5-methoxymethylideneamino-3-(1,2,4-oxadiazol-3-yl)-4-trifluoromethylsulfinylpyrazole

Product 1

HCID 183547715-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(1,2,4-oxadiazol-3-yl)-4-trifluoromethylsulfinylpyrazoleYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(2,6-Dichloro-4-trifluoromethylphenyl)-5-methoxymethylideneamino-3-(1,2,4-oxadiazol-3-yl)-4-trifluoromethylsulfinylpyrazole (151 mg, 0.29 mmol) was dissolved in 5 ml of acetone and 1.2 N hydrochloric acid (0.12 ml, 0.14 mmol) was added, and then the mixture was stirred at room temperature. Seven hours after stirring, 1.2 N hydrochloric acid (0.12 ml, 0.14 mmol) was further added, followed by stirring at room temperature for 3 days. Furthermore, 1.2 N hydrochloric acid (0.12 ml, 0.14 mmol) was added, followed by heating to 50° C. and stirring for another 9 hours. After 5 ml of water and 2 ml of an aqueous saturated sodium hydrogencarbonate solution were added, acetone was distilled off and extracted with 40 ml ethyl acetate. The ethyl acetate layer was washed twice with 30 ml of an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 136 mg (0.29 mmol) of the title compound as a yellowish crystal.

Workup

  1. stirringSeven hours after stirring
  2. stirringby stirring at room temperature for 3 days
  3. temperatureby heating to 50° C.
  4. stirringstirring for another 9 hours
  5. distillationacetone was distilled off
  6. extractionextracted with 40 ml ethyl acetate
  7. washThe ethyl acetate layer was washed twice with 30 ml of an aqueous saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-69f552fa3fb442f7ad12ab3020e355ec
Source dataset
uspto-grants-2001_11
Patent number
US06316477B1

Reaction notes

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