Water → 5-Chloro-2-nitro-4-phenoxyphenylamine

HRID 408700

반응식

HRID 408700 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[Na+].Cl[C:15]1[C:20]([Cl:21])=[CH:19][C:18]([NH2:22])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1.O>CN(C=O)C>[Cl:21][C:20]1[C:15]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:16][C:17]([N+:23]([O-:25])=[O:24])=[C:18]([NH2:22])[CH:19]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 996PhenolHCID 811494,5-Dichloro-2-nitroanilineHCID 23676156Sodium t-butoxide

생성물 1

HCID 669372525-Chloro-2-nitro-4-phenoxyphenylamine수율 64.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of phenol (0.500 g, 5.31 mmol) in dry DMF (20 mL) was added solid sodium t-butoxide (0.510 g, 5.31 mmol). The mixture was heated to 100° C. for 60 min, then 4,5-dichloro-2-nitro-phenylamine (1.00 g, 4.83 mmol) was added and the reaction mixture was heated at 100° C. for 19 h. The reaction mixture was allowed to cool to ambient temperature. The reaction mixture was added to water and extracted with EtOAc. The combined organic layers were washed with 1M Na2CO3, dried, filtered, and concentrated under reduced pressure. The residue was purified (FCC) (hexanes:EtOAc, 5% to 30% over 20 minutes) to yield the titled compound as an orange solid (0.821 g, 64%). 1H NMR (400 MHz, CDCl3): 8.27 (s, 1H), 7.50-7.34 (m, 2H), 7.27 (d, J=8.9 Hz, 2H), 7.10 (dd, J=8.6, 1.1 Hz, 2H), 6.02 (s, 3H).

후처리

  1. temperaturethe reaction mixture was heated at 100° C. for 19 h
  2. temperatureto cool to ambient temperature
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with 1M Na2CO3
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified (FCC) (hexanes:EtOAc, 5% to 30% over 20 minutes)

출처 및 근거

ORD 기록
ord-2ee9bf206ca04b949f494819f78a0719
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759345B2

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