Acetaminophen → N-[4-(3-Chloro-5-nitro-phenoxy)-phenyl]-acetamide

HRID 2197947노트

반응식

HRID 2197947 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[CH:3]=1.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1)[O:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:19][CH:20]=1

참가 물질

6

반응물 3

HCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 330981-Chloro-3,5-dinitrobenzene

생성물 1

HCID 68460873N-[4-(3-Chloro-5-nitro-phenoxy)-phenyl]-acetamide수율 92.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

The product from Example 193a (1.06 g, 5.2 mmol), N-(4-hydroxyphenyl)acetamide (0.70 g, 4.5 mmol) and K2CO3 (0.79 g, 5.7 mmol) in DMF (14 ml) was heated at 110° C. for 6 hours. The reaction mixture was cooled to room temperature, diluted with H2O and then extracted with EtOAc. The extract washed with H2O and brine, dried over MgSO4, filtered and concentrated under vacuum giving the crude title compound as a pale brown crystal, which was purified by washing with i-Pr2O to give the desired product as pale brown crystal (1.28 g, 92%).

후처리

  1. extractionextracted with EtOAc
  2. washThe extract washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customgiving the crude title compound as a pale brown crystal, which
  7. customwas purified
  8. washby washing with i-Pr2O

출처 및 근거

ORD 기록
ord-03c3545eada8456babb1c4b4d50bfdc6
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338605B2

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