Reacción #2467961

Ecuación de reacción

water

ammonium hydroxide

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

→

product

Rendimiento 72.0%

3-[(Dimethylamino)diazenyl]thiophene-2-carboxamide

Rendimiento 72.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Filtraciónthe precipitated solid was filtered
3. 3
   Otrodried
4. 4
   Otroto give crude product, which
5. 5
   Otrowas chromatographed over silica gel column

Procedimiento

To an ice cold (0-5° C.) solution of ammonium hydroxide (20 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (600 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 precipitated solid was filtered and dried to give crude product, which was chromatographed over silica gel column using chloroform-methanol (98:2) as eluents to give the product as an off-white solid (400 mg, 72%), mp 168-170° C. IR (neat) νmax 3337, 3172, 2923, 1636, 1599, 1348, 1219, 1117, 884, 771 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.28 (2H, br s), 7.35 (1H, d, J=5.6 Hz), 7.31 (1H, d, J=5.6 Hz), 3.58 (3H, br s), 3.20 (3H, br s); LC-MS (positive ion mode): m/z 221 (M+Na)+.

Fuente