반응 #2467979

반응 방정식

water

ethylenediamine

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

sodium chloride

→

product

수율 22.0%

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

수율 22.0%

용매

ethanol

ethanol

반응 조건

후처리

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   추출The solution was extracted with THF (3×100 mL)
3. 3
   세척The combined THF layer was washed with 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

실험 절차

To an ice cold (0-5° C.) solution of ethylenediamine (5 mL) in ethanol (5 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (250 mg) in ethanol (5 mL) for 5 min and stirred at rt for 24 h. The solution was poured into ice cooled water and saturated with sodium chloride. The solution was extracted with THF (3×100 mL). The combined THF layer was washed with 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 (90:10) as eluents to give the product as an off-white solid (60 mg, 22%), mp 98-100° C. 1H NMR (400 MHz, CDCl3): δ 8.65 (1H, br s), 7.30 (1H, d, J=5.2 Hz), 7.28 (1H, d, J=5.2 Hz), 3.50-3.57 (5H, m). 3.24 (3H, br s), 2.91 (2H, t, J=6.0 Hz).

출처