Reacción #2467978

Ecuación de reacción

water

methyl amine

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

→

solid

Rendimiento 76.0%

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

Rendimiento 76.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Extracciónthe solution was extracted with chloroform (3×100 mL)
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
8. 8
   Otroto give the product, which
9. 9
   Otrowas recrystallized from chloroform-hexane

Procedimiento

To an ice cold (0-5° C.) solution of methyl amine (3 mL) in THF (5 mL) was added a solution of methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (500 mg) in THF (5 mL) for 5 min and stirred at rt for 36 h. The solution was poured into ice cooled water and the solution was extracted with chloroform (3×100 mL). 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, which was recrystallized from chloroform-hexane gave the product as a pale orange color solid (380 mg, 76%), mp 98-102° C. IR (neat) νmax 3297, 3082, 2929, 1637, 1380, 1348, 1299, 1221, 1109, 1016, 882, 776 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.35 (1H, br s), 7.29 (1H, d, J=5.2 Hz), 7.27 (1H, d, J=5.2 Hz), 3.57 (3H, br s), 3.21 (3H, br s), 3.00 (3H, d, J=4.8 Hz); LC-MS (positive ion mode): m/z 213 (M+H)+.

Fuente