m-Chloroperbenzoic acid → N2-(1,1-dimethyl-2-methylsulfinyl ethyl)-3-iodo-N1-[2-methyl-4-{2,2,2-trifluoro-1-(trifluoromethyl)ethyl}phenyl]phthalamide

HRID 641131Notes

Reaction equation

[CH3:1][C:2]([NH:7][C:8](=[O:35])[C:9]1[C:10](=[CH:30][CH:31]=[CH:32][C:33]=1[I:34])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=1[CH3:29])=[O:12])([CH3:6])[CH2:3][S:4][CH3:5].ClC1C=CC=C(C(OO)=[O:44])C=1>C(Cl)(Cl)Cl>[CH3:6][C:2]([NH:7][C:8](=[O:35])[C:9]1[C:10](=[CH:30][CH:31]=[CH:32][C:33]=1[I:34])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:21]([F:23])([F:22])[F:24])[C:25]([F:28])([F:26])[F:27])=[CH:16][C:15]=1[CH3:29])=[O:12])([CH3:1])[CH2:3][S:4]([CH3:5])=[O:44]

Participants

Conditions

Temperature: 0 °C

Procedure

In 10 ml of chloroform was dissolved 0.63 g (1.0 mmol) of N2-(1,1-dimethyl-2-methylthioethyl)-3-iodo-N1-{2-methyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamide, and the resulting solution was cooled to 0° C. To the solution was added 0.19 g (1.1 mmol) of meta-chloroperbenzoic acid. After stirring for one hour, the reaction mixture was washed with 10% aqueous solution of potassium carbonate and dried on anhydrous magnesium sulfate, and the solvent was dissolved off under reduced pressure. Thus, 0.45 g of the objective compound was obtained (yield: 69%).

Workup

washthe reaction mixture was washed with 10% aqueous solution of potassium carbonate
dry with materialdried on anhydrous magnesium sulfate
dissolutionthe solvent was dissolved off under reduced pressure

Sources & evidence

ORD record: ord-09cc79ad106040d2a24e81c6650538aa
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696129B2

Reaction notes

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