Reaktion #2467978

Reaktionsgleichung

water

methyl amine

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

→

solid

Ausbeute 76.0%

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

Ausbeute 76.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Extraktionthe solution was extracted with chloroform (3×100 mL)
3. 3
   WaschenThe combined chloroform layer was washed with water, brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   FiltrationThe solution was filtered
6. 6
   Sonstigeevaporated the solvent
7. 7
   SonstigeThe residue was chromatographed over silica gel column
8. 8
   Sonstigeto give the product, which
9. 9
   Sonstigewas recrystallized from chloroform-hexane

Vorschrift

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)+.

Quelle