Ethyl Acetate → [4-(2-Amino-4-benzoylaminophenoxy)phenyl]carbamic acid tert-butyl ester

HRID 605266Notes

Reaction equation

HRID 605266 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][C:16]=2[N+:30]([O-])=O)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-].CCOC(C)=O.C([O-])(O)=O.[Na+]>C1COCC1.O.[Fe]>[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:29])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:17][C:16]=2[NH2:30])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 67040356[4-(4-Benzoylamino-2-nitrophenoxy)-phenyl]carbamic acid tert-butyl ester

Product 1

HCID 67040690[4-(2-Amino-4-benzoylaminophenoxy)phenyl]carbamic acid tert-butyl esterYield 95.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 252a (1.50 g, 3.3 mmol), Fe powder (0.78 g, 13.4 mmol) and NH4Cl (0.71 g, 13.4 mmol) in a mixture of THF (7.5 mL) and H2O (3 mL) was gradually heated to reflux and refluxed for 19 hours. The reaction mixture was portioned between EtOAc and 10% NaHCO3 and then filtered (through celite). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum giving the crude title compound which was purified by column chromatography on silica gel eluting with 1:1 n-hexane/EtOAc to give the title compound as a yellow foam (1.32 g, 94%).

Workup

  1. temperaturewas gradually heated
  2. temperatureto reflux
  3. temperaturerefluxed for 19 hours
  4. filtrationfiltered (through celite)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customgiving the crude title compound which
  10. customwas purified by column chromatography on silica gel eluting with 1:1 n-hexane/EtOAc

Sources & evidence

ORD record
ord-3426851cbbe84134a877d7cec839906d
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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