Reaktion #2467977

Reaktionsgleichung

water

ethanol amine

methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate

→

solid

Ausbeute 77.0%

{3-[(dimethylamino)diazenyl] (2-thienyl)}-N-(2-hydroxyethyl)-carboxamide

Ausbeute 77.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Extraktionthe solution was extracted with ethyl acetate (3×50 mL)
3. 3
   WaschenThe combined EtOAc layer was washed with water, brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   FiltrationThe solution was filtered
6. 6
   Sonstigeevaporated the solvent
7. 7
   SonstigeThe residue was chromatographed over silica gel column
8. 8
   Sonstigeto give the product, which
9. 9
   Sonstigewas recrystallized from chloroform-hexane

Vorschrift

To an ice cold (0-5° C.) solution of ethanol amine (5 mL) in THF (5 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (500 mg) in THF (5 mL) for 5 min and stirred at rt for 20 h. The solution was poured into ice cooled water and the solution was extracted with ethyl acetate (3×50 mL). The combined EtOAc layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using chloroform-methanol (95:5) as eluents to give the product, which was recrystallized from chloroform-hexane gave the product as a pale orange color solid (430 mg, 77%), mp 118-122° C. IR (neat) νmax, 3397, 3278, 2926, 1621, 1353, 1298, 1220, 1083, 1007, 882, 775 cm−1;

Quelle