Peracetic Acid → HCID 53723907, compound

HRID 1087946Notes

Reaction equation

HRID 1087946 reaction equation
[CH3:1][N:2]([CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]=1)=[CH2:16])[S:3]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:5])=[O:4].O.O.O.C([O-])(=[O:32])C.[Na+].C(OO)(=O)C>C(Cl)(Cl)Cl>[O:32]1[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:24])[F:26])[N:18]=2)([CH2:14][N:2]([CH3:1])[S:3]([CH:6]=[CH:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)(=[O:4])=[O:5])[CH2:16]1

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 23665404Sodium Acetate TrihydrateHCID 53653060HCID 53653060, compound

Product 1

HCID 53723907HCID 53723907, compoundYield 119.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.1 g of 3-(N-methyl-N-styrylsulfonylamino)-2-(6-trifluoromethylpyridin-2-yl)propene, 0.20 g of sodium acetate trihydrate, 2.19 g of 40% peracetic acid and 11 ml of chloroform was stirred at 60° C. for 5 hours. After the reaction mixture was cooled to room temperature, 10 ml of carbon tetrachrolide was added thereto, and the whole mixture was subsequently washed with water, an aqueous solution of 10% sodium bisulfite, a 2N aqueous solution of sodium hydroxide, water and saturated saline solution in that order and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by silica gel column chromatography (eluted with benzene-ethyl acetate 15:1) to obtain 0.70 g of Compound No. 4 in Table 1.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. addition10 ml of carbon tetrachrolide was added
  3. washthe whole mixture was subsequently washed with water
  4. dry with materialan aqueous solution of 10% sodium bisulfite, a 2N aqueous solution of sodium hydroxide, water and saturated saline solution in that order and dried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography (eluted with benzene-ethyl acetate 15:1)

Sources & evidence

ORD record
ord-16ec0bf3edfd4f4ca614ac403df4d15d
Source dataset
uspto-grants-1990_10
Patent number
US04960897

Reaction notes

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