Reacción #2467987

Ecuación de reacción

water

ammonium hydroxide

methyl 4-[(dimethylamino)diazenyl]thiophene-3-carboxylate

→

solid

Rendimiento 25.0%

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

Rendimiento 25.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Extracciónextracted with chloroform
3. 3
   LavadoThe combined chloroform 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 (5 mL) was added a solution of methyl 4-[(dimethylamino)diazenyl]thiophene-3-carboxylate (110 mg) in THF (2 mL) for 5 min and stirred at rt for 36 h. The solution was poured into ice cooled water and extracted with chloroform. The combined chloroform 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 chloroform-methanol (98:2) as eluents to give the product as a pale red color solid (25 mg, 25%), mp 168-172° C. IR (neat) νmax 3324, 3125, 2917, 2851, 1655, 1600, 1367, 1336, 1090 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.55 (1H, br s), 8.19 (1H, d, J=3.6 Hz), 7.15 (1H, d, J=3.6 Hz), 5.84 (1H, br s), 3.56 (3H, br s), 3.19 (3H, br s); LC-MS (positive ion mode): m/z 199 (M+H)+.

Fuente