N-Methylaniline → 4-Chloro-N-methyl-2-nitro-N-phenylphenylamine

HRID 16183

反応式

HRID 16183 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:19]([CH3:18])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

参加物

5

反応物 3

HCID 7515N-MethylanilineHCID 11430Potassium CarbonateHCID 676604-Chloro-1-fluoro-2-nitrobenzene

生成物 1

HCID 214144194-Chloro-N-methyl-2-nitro-N-phenylphenylamine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
180 °C

実験手順

4-Chloro-1-fluoro-2-nitrobenzene (20.0 g, 0.11 mol) and K2CO3 (15.7 g, 0.11 mol) were dissolved in N-methylaniline (37 mL, 0.34 mol) and subsequently heated to 180° C. After 5 h, the reaction mixture was cooled to room temperature, diluted with CH2Cl2 (750 mL) and washed with H2O (500 mL), aq. citric acid (5% 500 mL) and brine (500 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The residual oil was chromatographed over silica (cyclohexane/CH2Cl2, 9/1, v/v) giving title compound containing ˜30% starting material. The compound was subsequently stirred in cold hexane and the resulting red crystals were filtered resulting in pure crystalline product (16.5 g, 57% yield). Data: melting point: 59-62° C., Rf 0.65 (cyclohexane/ethyl acetate, 4/1, v/v).

後処理

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washwashed with H2O (500 mL), aq. citric acid (5% 500 mL) and brine (500 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residual oil was chromatographed over silica (cyclohexane/CH2Cl2, 9/1

出典と根拠

ORDレコード
ord-6d9b7558ab0740298d5cb9ab08c3764e
出典データセット
uspto-grants-2010_06
特許番号
US07737136B2

関連ノート

読み込み中…