Potassium Carbonate → N,N-dimethyl-5-methyl-2-(2',4'-dichloro-6'-methylanilino)phenylacetamide

HRID 1280837Notes

Reaction equation

HRID 1280837 reaction equation
[CH3:1][N:2]([CH3:14])[C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1I.[Cl:15][C:16]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([CH3:24])[C:17]=1[NH2:18].C(=O)([O-])[O-].[K+].[K+]>[Cu].[Cu]I>[CH3:1][N:2]([CH3:14])[C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[NH:18][C:17]1[C:19]([CH3:24])=[CH:20][C:21]([Cl:23])=[CH:22][C:16]=1[Cl:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12682872,4-Dichloro-6-methylanilineHCID 15541938N,N-dimethyl-5-methyl-2-iodophenylacetamide

Product 1

HCID 15541937N,N-dimethyl-5-methyl-2-(2',4'-dichloro-6'-methylanilino)phenylacetamide

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

N,N-Dimethyl-5-methyl-2-iodophenylacetamide (3.5 g, 11.5 mmol) and 2,4-dichloro-6-methylaniline (4.1 g, 23 mmol) are stirred in xylenes (100 ml) with copper powder (0.18 g, 2.9 mmol), copper(I) iodide (0.55 g, 2.9 mmol) and anhydrous potassium carbonate (1.6 g, 11.5 mmol). The reaction is heated to reflux temperature for 48 hours. While still slightly warm (40°) the brown suspension is filtered through a pad of Celite, which in turn is rinsed with toluene (75 ml). The filtrate is evaporated on a rotovap and flash chromatographed on silica gel (Rf 0.30 in 40% EtOAc/hexane) to give N,N-dimethyl-5-methyl-2-(2′,4′-dichloro-6′-methylanilino)phenylacetamide as an off-white crystalline solid, m.p. 119-124°.

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux temperature for 48 hours
  3. temperatureWhile still slightly warm (40°) the brown suspension
  4. filtrationis filtered through a pad of Celite, which in turn
  5. washis rinsed with toluene (75 ml)
  6. customThe filtrate is evaporated on a rotovap and flash
  7. customchromatographed on silica gel (Rf 0.30 in 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-7e92218065c44883964999416372285c
Source dataset
uspto-grants-2002_09
Patent number
US06451858B2

Reaction notes

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