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

HRID 1596638ノート

反応式

HRID 1596638 の反応式
[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].[I-].C(=O)([O-])[O-].[K+].[K+]>[Cu]>[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]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 12682872,4-Dichloro-6-methylanilineHCID 15541938N,N-dimethyl-5-methyl-2-iodophenylacetamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 23978Copper触媒2 回

実験手順

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(l) 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°.

後処理

  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)

出典と根拠

ORDレコード
ord-c650486d9a7249e7b1508c664dddde4b
出典データセット
uspto-grants-2001_09
特許番号
US06291523B1

反応ノート

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