Reacción #2467966

Ecuación de reacción

water

ammonium hydroxide

methyl 3-[(dimethylamino)diazenyl]-5-nitrothiophene-2-carboxylate

→

solid

Rendimiento 26.0%

3-[(Dimethylamino)diazenyl]-5-nitrothiophene-2-carboxamide

Rendimiento 26.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Extracciónextracted with ethyl acetate (3×100 mL)
3. 3
   LavadoThe combined organic layer was washed with water, 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 ammonium hydroxide (35 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]-5-nitrothiophene-2-carboxylate (400 mg) in THF (10 mL) for 5 min and stirred at rt for 20 h. The solution was poured into ice cooled water and extracted with ethyl acetate (3×100 mL). The combined organic 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 hexane-ethyl acetate (50:50) as eluents to give the product as a yellow color solid (90 mg, 26%), mp 240-246° C. 1H NMR (400 MHz, DMSO-d6): δ 8.22 (1H, s), 8.05 (1H, s), 7.91 (1H, s), 3.63 (3H, s), 3.26 (3H, s); LC-MS (positive ion mode): m/z 266 (M+Na)+.

Fuente