反応 #2467979

反応方程式

water

ethylenediamine

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

sodium chloride

→

product

収率 22.0%

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

収率 22.0%

溶媒

ethanol

ethanol

反応条件

後処理

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   抽出The solution was extracted with THF (3×100 mL)
3. 3
   洗浄The combined THF layer was washed with brine
4. 4
   乾燥dried over sodium sulfate
5. 5
   ろ過The solution was filtered
6. 6
   その他evaporated the solvent
7. 7
   その他The residue was chromatographed over silica gel column

実験手順

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).

出典