Monomethyl terephthalate → 4-(Hydrazinocarbonyl)benzoic acid

HRID 1093771

Reaktionsgleichung

Reaktionsgleichung von HRID 1093771
O.[NH2:2][NH2:3].C[O:5][C:6](=O)[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1>CO>[NH:2]([C:6]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)=[O:5])[NH2:3]

Komponenten

4

Edukt 2

HCID 15513Monomethyl terephthalateHCID 24654Hydrazine hydrate (1:1)

Produkt 1

HCID 2794374-(Hydrazinocarbonyl)benzoic acidAusbeute 90,09 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Hydrazine hydrate was added to a solution of terephthalic acid monomethyl ester (1 g, 5.5 mmol) in MeOH (10 mL) and stirring was continued for 1 hr. The reaction mixture was concentrated to afford 900 mg (90.09% Yield) of 4-hydrazinocarbonyl-benzoic acid. p-Toluene sulfonic acid (48 mg, 0.277 mmol) was added to a solution of 4-hydrazinocarbonyl-benzoic acid (500 mg, 2.77 mmol) in triethylorthoformate (7.5 mL, 44.0 mmol) and stirring was continued with heating at 100° C. for 3 hrs. The reaction mixture was diluted with water, the solid was collected to afford 200 mg (37.9% Yield) of 4-[1,3,4]oxadiazol-2-yl-benzoic acid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-96d3309410914684b749c5c0cfc814d6
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129376B2

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