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

HRID 16183

반응식

HRID 16183 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
180 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6d9b7558ab0740298d5cb9ab08c3764e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737136B2

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