Potassium Carbonate → N,N-Dimethyl-2-(2',3',5',6'-tetrafluoro-4'-phenylanilino)phenylacetamide

HRID 1270798Notes

Reaction equation

[CH3:1][N:2]([CH3:13])[C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1I.[F:14][C:15]1[C:21]([F:22])=[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]([F:29])=[C:18]([F:30])[C:16]=1[NH2:17].C(=O)([O-])[O-].[K+].[K+]>[Cu].[Cu]I>[CH3:1][N:2]([CH3:13])[C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:17][C:16]1[C:18]([F:30])=[C:19]([F:29])[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:21]([F:22])[C:15]=1[F:14]

Participants

Conditions

Temperature: 40 °C

Procedure

N,N-dimethyl-2-iodophenylacetamide (2.0 g, 6.9 mmol), 2,3,5,6-tetrafluoro-4-phenylaniline (3.3 g, 13.8 mmol), copper powder (219 mg, 3.4 mmol), copper(I) iodide (646 mg, 3.4 mmol) and anhydrous potassium carbonate (1.0 g, 6.9 mmol) are stirred together in 150 mL of xylenes. The reaction is heated to reflux temperature for 48 hours. While still slightly warm (40° C.) the brown suspension is filtered through a pad of Celite which in turn is rinsed with toluene (250 mL). The filtrate is evaporated by rotary evaporator and then flash chromatographed on silica gel (10–20% EtOAc/hexane) to give the title product.

Workup

temperatureThe reaction is heated
temperatureto reflux temperature for 48 hours
filtrationis filtered through a pad of Celite which in turn
washis rinsed with toluene (250 mL)
customThe filtrate is evaporated by rotary evaporator
customflash chromatographed on silica gel (10–20% EtOAc/hexane)

Sources & evidence

ORD record: ord-9f4e363e919b4b91833a344c85689802
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202364B2

Reaction notes

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