반응 #2467977

반응 방정식

water

ethanol amine

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

→

solid

수율 77.0%

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

수율 77.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   추출the solution was extracted with ethyl acetate (3×50 mL)
3. 3
   세척The combined EtOAc layer was washed with water, brine
4. 4
   건조dried over sodium sulfate
5. 5
   여과The solution was filtered
6. 6
   기타evaporated the solvent
7. 7
   기타The residue was chromatographed over silica gel column
8. 8
   기타to give the product, which
9. 9
   기타was recrystallized from chloroform-hexane

실험 절차

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;

출처