Potassium Hydroxide → HCID 67041089, compound

HRID 605276Notes

Reaction equation

HRID 605276 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[S:12][C:13]([Br:16])=[CH:14][CH:15]=2)=[O:10])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[OH-].[K+].[C:22]([O:26][C:27](=[O:36])[NH:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)([CH3:25])([CH3:24])[CH3:23]>CN(C=O)C.O>[C:22]([O:26][C:27](=[O:36])[NH:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]3[S:12][C:13]([Br:16])=[CH:14][CH:15]=3)=[O:10])=[CH:4][C:3]=2[N+:17]([O-:19])=[O:18])=[CH:33][CH:34]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 2649530HCID 2649530, compoundHCID 2756771N-Boc-4-hydroxyaniline

Product 1

HCID 67041089HCID 67041089, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The product of Example 241b (1.50 g, 4.34 mmol) was dissolved in DMF to which KOH (469 mg, 8.69 mmol), and (4-Hydroxy-phenyl)-carbamic acid tert-butyl ester (909 mg, 4.34 mmol) were added. The reaction mixture was then heated to 80° C. for 2 hrs. At this point the reaction mixture was cooled to room temperature and diluted with water that was then extracted with ethyl acetate. Dried over Na2SO4, filtered and concentrated under vacuum giving the title compound to provide the title compound (2.11 g, 90%).

Workup

  1. additionwere added
  2. temperatureAt this point the reaction mixture was cooled to room temperature
  3. extractionwas then extracted with ethyl acetate
  4. dry with materialDried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-85c67ba3cdad4f08977aa02b96ad1518
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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