Hydrogen Peroxide → N-(2-methylsulfinyl-1,1-dimethyl-ethyl)-N'-(2-methyl-4-(1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl)phenyl)phthalamide

HRID 2358869Notes

Reaction equation

HRID 2358869 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4](Cl)=[O:5].[OH-].[Na+].[CH3:15][C:16]([NH2:21])([CH3:20])[CH2:17][S:18][CH3:19].C1(=O)NC(=[O:28])C2=CC=CC1=C2.OO.[CH3:35][C:36]1[CH:42]=[C:41]([C:43]([F:52])([C:48]([F:51])([F:50])[F:49])[C:44]([F:47])([F:46])[F:45])[CH:40]=[CH:39][C:37]=1[NH2:38].S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.ClCCCl>[CH3:15][C:16]([NH:21][C:1]([C:2]1[C:3]([C:4]([NH:38][C:37]2[CH:39]=[CH:40][C:41]([C:43]([F:52])([C:44]([F:46])([F:47])[F:45])[C:48]([F:49])([F:50])[F:51])=[CH:42][C:36]=2[CH3:35])=[O:5])=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:11])([CH3:20])[CH2:17][S:18]([CH3:19])=[O:28]

Participants

11

Reactant 8

HCID 784Hydrogen PeroxideHCID 6955Phthaloyl chlorideHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 99255434-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)-2-methylanilineHCID 120973802-Propanamine, 2-methyl-1-(methylthio)-HCID 18926764Isophthalimide

Product 1

HCID 22066255N-(2-methylsulfinyl-1,1-dimethyl-ethyl)-N'-(2-methyl-4-(1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl)phenyl)phthalamideYield 83%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

Phthaloyl dichloride (18.78 g) was added dropwise to a mixture of aqueous sodium hydroxide solution (7.59 g/55 mL), 2-methyl-1-methylthio-2-propanamine (11.03 g) and 1,2-dichloroethane (55 mL) at 40° C. or lower. After completion of the dropwise addition, the resulting mixture was stirred at 40° C. for 30 minutes and the organic layer was separated to prepare a solution of N-[1,1-dimethyl-2-(methylthio)ethyl]isophthalimide in 1,2-dichloroethane. The previously prepared isophthalimide solution and 35% hydrogen peroxide (9.89 g) were slowly dropped at the same time into a mixture of 2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline (24.18 g), p-toluenesulfonic acid monohydrate (0.44 g) and 1,2-dichloroethane (13.75 mL) at 60° C. and then stirred at 60° C. for 1 hour. An aqueous sodium sulfite solution was added dropwise to the thus obtained reaction mixture at the same temperature to decompose the excess oxidizing agent. Then, the resulting mixture was neutralized with an aqueous sodium hydrogencarbonate solution, after which the organic layer was separated. The organic layer obtained was slowly cooled to 20° C. The crystals precipitated were filtered, washed with water and then dried to obtain 41.70 g (yield 83%) of the title compound.

Workup

  1. additionAfter completion of the dropwise addition
  2. customthe organic layer was separated
  3. customto prepare a solution of N-[1,1-dimethyl-2-(methylthio)ethyl]isophthalimide in 1,2-dichloroethane
  4. stirringstirred at 60° C. for 1 hour
  5. customafter which the organic layer was separated
  6. customThe organic layer obtained
  7. temperaturewas slowly cooled to 20° C
  8. customThe crystals precipitated
  9. filtrationwere filtered
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-020f1056a1f641648f180fd1382bf905
Source dataset
uspto-grants-2010_07
Patent number
US07763750B2

Reaction notes

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