Sodium Hydroxide → 3-[(4-methoxybenzoyl)amino]-4-[(4-tert-butylbenzoyl)amino]benzoic Acid

HRID 427648Notes

Reaction equation

HRID 427648 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=2[NH:20][C:21](=[O:32])[C:22]2[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=2)[C:13]([O:15]C)=[O:14])=[O:8])=[CH:5][CH:4]=1.[OH-].[Na+]>O1CCCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=2[NH:20][C:21](=[O:32])[C:22]2[CH:23]=[CH:24][C:25]([C:28]([CH3:30])([CH3:31])[CH3:29])=[CH:26][CH:27]=2)[C:13]([OH:15])=[O:14])=[O:8])=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 10742629Methyl 3-[(4-methoxybenzoyl)amino]-4-[(4-tert-butylbenzoyl)amino]benzoate

Product 1

HCID 108132673-[(4-methoxybenzoyl)amino]-4-[(4-tert-butylbenzoyl)amino]benzoic AcidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[(4-methoxybenzoyl)amino]-4-[(4-tert-butylbenzoyl)amino]benzoate (0.487 g, 1.00 mmol) in tetrahydrofuran (32 mL) and methanol (8 mL) was added 5 N aqueous sodium hydroxide (0.6 mL). The resulting mixture was stirred for 16 h, a second portion of 5 N aqueous sodium hydroxide (0.6 mL) added, and the mixture stirred for an additional 16 h. The solvent was concentrated in vacuo and the crude product acidified with dilute aqueous hydrochloric acid and diluted with ethyl acetate. The mixture was extracted with saturated aqueous potassium carbonate solution. The aqueous layer was acidified and extracted with ethyl acetate. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. Crystallization of the residue from methylene chloride/-hexane provided 376 mg (100%) of the title product.

Workup

  1. stirringthe mixture stirred for an additional 16 h
  2. concentrationThe solvent was concentrated in vacuo
  3. additiondiluted with ethyl acetate
  4. extractionThe mixture was extracted with saturated aqueous potassium carbonate solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customCrystallization of the residue from methylene chloride/-hexane

Sources & evidence

ORD record
ord-fcc18f7a2ce74976afe11778d74b269c
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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