Reaktion #1696018

Reaktionsgleichung

2-amino-N-[2-(1H-imidazol-2-yl)-ethyl] benzene sulfonamide

oxalic acid

meta-t-butylbenzoyl chloride

→

desired titled compound

Ausbeute 84.2%

N-[2-[[[2-(1H-Imidazol-2-yl)ethyl]amino]sulfonyl]phenyl]-3-(1,1-dimethylethyl)benzamide oxalate

Ausbeute 84.2%

Lösungsmittel

methanol

methanol

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe titled compound was prepared substantially in accordance with the method
2. 2
   TemperaturThe resulting solution was heated
3. 3
   Temperaturto reflux for approximately one hour
4. 4
   SonstigeThe resulting layers were separated
5. 5
   Waschenthe organic layer was washed with water
6. 6
   Trocknena saturated sodium chloride solution, dried over anhydrous sodium sulfate
7. 7
   SonstigeThe resultant residue was purified
8. 8
   workup.ADDITIONFractions containing the free base form of the desired titled compound
9. 9
   Sonstigeto provide an oil
10. 10
    Sonstigeto provide a foam
11. 11
    SonstigeThis foam was crystallized from a 1:10 solution of methanol/ethyl acetate

Vorschrift

The titled compound was prepared substantially in accordance with the method detailed in Example 1C using 2.80 g (0.0107 mol) of 2-amino-N-[2-(1H-imidazol-2-yl)-ethyl] benzene sulfonamide and 4.20 g (0.0213 mol) of meta-t-butylbenzoyl chloride with the exception that, after reducing the reaction solution to dryness under reduced pressure the resultant residue was dissolved in methanol. The resulting solution was heated to reflux for approximately one hour and then reduced to dryness under reduced pressure. The resultant residue was redissolved in an ethyl acetate/aqueous sodium bicarbonate mixture. The resulting layers were separated and the organic layer was washed with water and then a saturated sodium chloride solution, dried over anhydrous sodium sulfate and then reduced to dryness under reduced pressure. The resultant residue was purified using preparatory high performance liquid chromatography (8000 ml of a gradient of methylene chloride to 10% methanol and 0.5% ammonium hydroxide in methylene chloride). Fractions containing the free base form of the desired titled compound were combined and then reduced to dryness under reduced pressure to provide an oil. This oil was dissolved in methanol and 0.36 g of oxalic acid were added, with stirring. The resulting solution was reduced to dryness under reduced pressure to provide a foam. This foam was crystallized from a 1:10 solution of methanol/ethyl acetate to provide 1.74 g of the desired titled compound (m.p. 191°-193.5° C.).

Quelle