Reaktion #2467961

Reaktionsgleichung

water

ammonium hydroxide

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

→

product

Ausbeute 72.0%

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

Ausbeute 72.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe solution was poured into ice
2. 2
   Filtrationthe precipitated solid was filtered
3. 3
   Sonstigedried
4. 4
   Sonstigeto give crude product, which
5. 5
   Sonstigewas chromatographed over silica gel column

Vorschrift

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)+.

Quelle