Toluene → 4-amino-3-chloro-N-[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl] benzamide

HRID 587847Notes

Reaction equation

C1(C)C=CC=CC=1.[Cl:8]N1C(=O)CCC1=O.[NH2:16][C:17]1[CH:43]=[CH:42][C:20]([C:21]([NH:23][C:24]2[C:29]([Cl:30])=[CH:28][C:27]([C:31]([F:40])([C:36]([F:39])([F:38])[F:37])[C:32]([F:35])([F:34])[F:33])=[CH:26][C:25]=2[Cl:41])=[O:22])=[CH:19][CH:18]=1>O>[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([NH:23][C:24]2[C:25]([Cl:41])=[CH:26][C:27]([C:31]([F:40])([C:36]([F:37])([F:38])[F:39])[C:32]([F:33])([F:34])[F:35])=[CH:28][C:29]=2[Cl:30])=[O:22])=[CH:42][C:43]=1[Cl:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To the toluene (30 ml) solution in which 4-amino-N-[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoro propan-2-yl)phenyl]benzamide (2.80 g) is dissolved, N-chlorosuccinimide (0.87 g) was added. The reaction solution was stirred for 6 hours at 80° C. under heating. The solution was cooled to room temperature, diluted with water and extracted twice with ethyl acetate. The organic phases were combined, and then dried over magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off under reduced pressure to obtain a crude product, which was then separated and purified by column chromatography to give 4-amino-3-chloro-N-[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl] benzamide (2.03 g, yield 67.3%).

Workup

temperatureunder heating
temperatureThe solution was cooled to room temperature
extractionextracted twice with ethyl acetate
dry with materialdried over magnesium sulfate
customThe drying agent was removed by filtration
distillationthe solvent was distilled off under reduced pressure
customto obtain a crude product, which
customwas then separated
custompurified by column chromatography

Sources & evidence

ORD record: ord-24867eb1c6f44d5db93ec0d1e35f976c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227923B2

Reaction notes

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