Reacción #2467979

Ecuación de reacción

water

ethylenediamine

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

sodium chloride

→

product

Rendimiento 22.0%

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

Rendimiento 22.0%

Disolventes

ethanol

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   ExtracciónThe solution was extracted with THF (3×100 mL)
3. 3
   LavadoThe combined THF layer was washed with brine
4. 4
   Secadodried over sodium sulfate
5. 5
   FiltraciónThe solution was filtered
6. 6
   Otroevaporated the solvent
7. 7
   OtroThe residue was chromatographed over silica gel column

Procedimiento

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).

Fuente