Water → 2-chloro-N-(2,6-diiodo-4-(perfluoropropan-2-yl)phenyl)-3-nitrobenzamide

HRID 590911Notes

Reaction equation

[I:1][C:2]1[CH:8]=[C:7]([C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([I:19])[C:3]=1[NH2:4].[Cl:20][C:21]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].O>CN1C(=O)N(C)CC1>[Cl:20][C:21]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH:4][C:3]1[C:2]([I:1])=[CH:8][C:7]([C:9]([F:18])([C:10]([F:13])([F:12])[F:11])[C:14]([F:15])([F:16])[F:17])=[CH:6][C:5]=1[I:19])=[O:24]

Participants

Conditions

Temperature: 135 °C

Procedure

To a solution of 40.0 g (78.0 mmol) of 2,6-diiodo-4-(perfluoropropan-2-yl)aniline in 100 ml of DMI was added 20.6 g (94.0 mmol) of 2-chloro-3-nitrobenzoyl chloride, followed by stirring at 135° C. for 3 hours. After cooling to room temperature, the reaction mixture was poured into 1000 ml of water. After extraction with the addition of 1000 ml of ethyl acetate, the organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was washed with hexane to prepare 56.2 g (yield 99%) of a target compound.

Workup

temperatureAfter cooling to room temperature
extractionAfter extraction
additionwith the addition of 1000 ml of ethyl acetate
washthe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
washthe obtained residue was washed with hexane

Sources & evidence

ORD record: ord-7148328b6a284a9390d4c273107ce80a
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09237745B2

Reaction notes

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