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

HRID 2358870Notes

Reaction equation

HRID 2358870 reaction equation
[OH-].[Na+].C(=O)([O-])O.[Na+].[CH3:8][C:9]([NH2:14])([CH3:13])[CH2:10][S:11][CH3:12].[C:15](Cl)(=[O:25])[C:16]1[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:18](Cl)=[O:19].C1(=O)NC(=[O:33])C2=CC=CC1=C2.OO.[CH3:40][C:41]1[CH:47]=[C:46]([C:48]([F:57])([C:53]([F:56])([F:55])[F:54])[C:49]([F:52])([F:51])[F:50])[CH:45]=[CH:44][C:42]=1[NH2:43].S([O-])([O-])=O.[Na+].[Na+]>O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.ClCCCl>[CH3:8][C:9]([NH:14][C:15]([C:16]1[C:17]([C:18]([NH:43][C:42]2[CH:44]=[CH:45][C:46]([C:48]([F:57])([C:49]([F:51])([F:52])[F:50])[C:53]([F:54])([F:55])[F:56])=[CH:47][C:41]=2[CH3:40])=[O:19])=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:25])([CH3:13])[CH2:10][S:11]([CH3:12])=[O:33]

Participants

12

Reactant 8

HCID 784Hydrogen PeroxideHCID 6955Phthaloyl chlorideHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium Bicarbonate2×HCID 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 80%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Sodium hydroxide (17.78 g) and sodium hydrogencarbonate (35.57 g) were dissolved in water (253 mL), followed by adding thereto 2-methyl-1-methylthio-2-propanamine (53 g) and 1,2-dichloroethane (253 mL), and to the resulting mixture was added dropwise phthaloyl dichloride (85.95 g) 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 (45.27 g) were slowly dropped at the same time into a mixture of 2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-aniline (110.7 g), p-toluenesulfonic acid monohydrate (2.01 g) and 1,2-dichloroethane (40 mL) at 60° C. and then stirred at 60° C. for 3 hours. 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 184.11 g (yield 80%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-3bf8705c842e4ab3b8ca5d1206c104b2
Source dataset
uspto-grants-2010_07
Patent number
US07763750B2

Reaction notes

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