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

HRID 605050

Reaction equation

HRID 605050 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-eefdb5c753664102b1343ff39b8b185a
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Linked notes

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