Sodium Hydroxide → 2,3-Bis[(4-methoxybenzoyl)amino]phenol

HRID 395807Notes

Reaction equation

HRID 395807 reaction equation
COC1C=CC(C(O[O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:18](=[O:27])[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[C:12]=2[NH:28][C:29](=[O:38])[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=O)=CC=1.[OH-].[Na+]>CO>[CH3:37][O:36][C:33]1[CH:32]=[CH:31][C:30]([C:29]([NH:28][C:12]2[C:13]([NH:17][C:18](=[O:27])[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:14][CH:15]=[CH:16][C:11]=2[OH:10])=[O:38])=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18174608HCID 18174608, compound

Product 1

HCID 106442072,3-Bis[(4-methoxybenzoyl)amino]phenolYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,3-bis[(4-methoxybenzoyl)amino]phenoxy 4-methoxybenzoate (7.75 g, 14.7 mmol) in methanol (100 mL) was cooled to ice-water bath temperature and 5 N aqueous sodium hydroxide solution (3.0 mL) was added. The reaction mixture was allowed to warm to room temperature and stirred for 72 hr. The reaction mixture was concentrated in vacuo and the resulting solid was dissolved in methylene chloride and washed with dilute aqueous hydrochloric acid, water, and saturated sodium chloride solution. The organic layer was dried (sodium sulfate), filtered, and concentrated in vacuo. Recrystallization of the residue from diethyl ether/hexane gave 2.3 g (40%) of the title product. mp 208-209° C.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe resulting solid was dissolved in methylene chloride
  4. washwashed with dilute aqueous hydrochloric acid, water, and saturated sodium chloride solution
  5. dry with materialThe organic layer was dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customRecrystallization of the residue from diethyl ether/hexane

Sources & evidence

ORD record
ord-44301514b7b2450687753a7b1982651e
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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