Water → [4-(4-Benzoylamino-2-nitrophenoxy)-phenyl]carbamic acid tert-butyl ester

HRID 605265

반응식

HRID 605265 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[C:20]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[OH-].[K+].O>CS(C)=O>[C:23]([O:22][C:20](=[O:21])[NH:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][C:3]=2[N+:17]([O-:19])=[O:18])=[CH:32][CH:33]=1)([CH3:26])([CH3:24])[CH3:25]

참가 물질

6

반응물 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 2756771N-Boc-4-hydroxyanilineHCID 3535228N-(4-fluoro-3-nitrophenyl)benzamide

생성물 1

HCID 67040356[4-(4-Benzoylamino-2-nitrophenoxy)-phenyl]carbamic acid tert-butyl ester수율 93.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
80 °C

실험 절차

A mixture of N-(4-fluoro-3-nitrophenyl)benzamide (1.00 g, 3.8 mmol), N-Boc-4-hydroxyaniline (0.83 g, 3.8 mmol) and 85% KOH (0.51 g, 7.7 mmol) in DMSO (20 mL) was heated at 80° C. for 1 hour, and then poured into H2O (100 ml) under stirring. The resulting oily crystal was extracted with EtOAc. The extract was washed with H2O (3 times) and brine, dried over MgSO4, filtered and concentrated under vacuum giving the crude title compound, which was purified by washing with i-Pr2O to give the desired compound as yellow crystals (1.59 g, 92%).

후처리

  1. extractionThe resulting oily crystal was extracted with EtOAc
  2. washThe extract was washed with H2O (3 times) and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customgiving the crude title compound, which
  7. customwas purified
  8. washby washing with i-Pr2O

출처 및 근거

ORD 기록
ord-0346ac4040c94a799838694124054c87
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

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