Potassium Carbonate → {4-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenoxy]phenyl}-carbamic acid tert-butyl ester

HRID 605050

반응식

HRID 605050 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13](Cl)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)=[CH:4][CH:3]=1.[C:21]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:24]([O:23][C:21](=[O:22])[NH:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][C:13]2[CH:14]=[CH:15][C:10]([C:9](=[O:20])[NH:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[CH:11][C:12]=2[N+:17]([O-:19])=[O:18])=[CH:33][CH:34]=1)([CH3:27])([CH3:25])[CH3:26]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1068537N-(4-bromophenyl)-4-chloro-3-nitrobenzamideHCID 2756771N-Boc-4-hydroxyaniline

생성물 1

HCID 67040702{4-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenoxy]phenyl}-carbamic acid tert-butyl ester수율 97%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of the product of Example 10A (5.132 g, 14.45 mmol) in anhydrous N,N-dimethylformamide (50 mL) was treated with N-Boc-4-hydroxyaniline (3.024 g, 14.45 mmol) and potassium carbonate (3.994 g, 28.90 mmol) at room temperature, then heated at 80° under a nitrogen atmosphere for 4.5 hours. The reaction was cooled to room temperature and the solvent removed by rotary evaporation in vacuo. The residue was taken up in ethyl acetate (200 mL) and washed with water (4×50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation to give the product as a dark yellow solid (7.38 g, 13.97 mmol, 97%).

후처리

  1. temperatureheated at 80° under a nitrogen atmosphere for 4.5 hours
  2. customthe solvent removed by rotary evaporation in vacuo
  3. washwashed with water (4×50 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-eefdb5c753664102b1343ff39b8b185a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

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