Acetic Anhydride → N-[4-[1-(1H-imidazol-1-yl)ethyl]phenyl]formamide

HRID 1723123

Reaktionsgleichung

[N:1]1([CH:6]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:15]([O-])=[O:16].[Na+].C(OC(=O)C)(=O)C>C(O)=O>[N:1]1([CH:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]=[O:16])=[CH:10][CH:9]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

(a-4) To a stirred solution of 15 parts of 4-[1-(1H-imidazol-1-yl)ethyl]-benzenamine and 2.7 parts of sodium formate in 60 parts of formic acid is added dropwise a solution of 9 parts of acetic acid anhydride in 24 parts of formic acid at 50° C. The reaction mixture was stirred for 1 hour at 100° C. and the solvent was evaporated. The residue was dissolved in a small amount of ice water and the solution was treated with ammonium hydroxide while cooling. The product was extracted twice with dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was crystallized twice from tetrahydrofuran, yielding 13.8 parts (80%) of N-[4-[1-(1H-imidazol-1-yl)ethyl]phenyl]-formamide; mp. 129.4° C. (int. 115).

Aufarbeitung

customthe solvent was evaporated
dissolutionThe residue was dissolved in a small amount of ice water
additionthe solution was treated with ammonium hydroxide
temperaturewhile cooling
extractionThe product was extracted twice with dichloromethane
customThe combined extracts were dried
filtrationfiltered
customevaporated
customThe residue was crystallized twice from tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag: ord-7376947100e44175beb11a11710ceb16
Quelldatensatz: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04859684

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