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

HRID 427648
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 427648
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fcc18f7a2ce74976afe11778d74b269c
Quelldatensatz
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06313122B1

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